Glycoscience: Biology and Medicine

Naoyuki Taniguchi • Tamao EndoGerald W. Hart • Peter H. SeebergerChi-Huey WongEditors

Glycoscience: Biologyand Medicine

With 333 Figures and 54 Tables

EditorsNaoyuki TaniguchiSystems Glycobiology Research GroupRIKEN-Max Planck Joint ResearchCenter for Systems Chemical BiologyGlobal Research ClusterRIKEN, Saitama, Japan

and

Osaka UniversityOsaka, Japan

Tamao EndoTokyo Metropolitan Institute ofGerontologyTokyo Metropolitan GeriatricHospital and Institute of GerontologyTokyo, Japan

Gerald W. HartDepartment of Biological ChemistryJohns Hopkins University Schoolof MedicineBaltimore, MD, USA

Peter H. SeebergerMax-Planck Institute for Colloidsand InterfacesDepartment of Biomolecular SystemsPotsdam, Germany

and

Freie Universit€at BerlinInstitute of Chemistry and BiochemistryBerlin, Germany

Chi-Huey WongAcademia SinicaNanKang, Taipei, Taiwan

and

The Scripps Research InstituteLa Jolla, CA, USA

ISBN 978-4-431-54840-9 ISBN 978-4-431-54841-6 (eBook)ISBN 978-4-431-54842-3 (print and electronic bundle)DOI 10.1007/978-4-431-54841-6Springer Tokyo Heidelberg New York Dordrecht London

Library of Congress Control Number: 2014953828

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ToThe late Yoshitaka Nagai,Professor Emeritus of the University of Tokyoand the first President of the JapanConsortium for Glycobiology andGlycotechnology (JCGG),who passed away on June 23, 2014

Preface

There is no doubt that glycoscience plays a pivotal role in various fields of research

in the life sciences. Scientists in other research fields realize this and frequently take

advantage of the various techniques that have been developed in glycoscience in

their research. However, for those who are not familiar with glycoscience and for

nonexperts in this field, this can be a daunting task.

The above is evident from the 2012 report issued by the US National Academy

of Sciences entitled “Transforming Glycoscience: A Road Map for the Future,”

which emphasizes the role of glycans in health, energy, and materials science. This

report concluded that the glycoscience community has had a substantial impact on

progress in the field of biomedical science. However, the feeling exists that the role

of energy and materials in glycoscience is still a difficult area of research from the

standpoint of glycobiology. On the other hand, regarding the role of glycoscience in

health and disease, enormous advances have been made in the field. This is

evidenced by the identification of new types of biomarkers for diseases and the

development of glycan-based therapeutics for the treatment of various diseases

such as infectious diseases, congenital disorders of glycosylation, autoimmune

diseases, cancer, degenerative neuromuscular diseases, and lifestyle-related

diseases such as diabetes and COPD. Alterations in the structure and function of

glycans in relation to disease, however, remain still to be clarified. Therefore,

further work based on basic biology research continues to be important. The current

increased focus on clinical applications may shift away from “curiosity-driven

research” or “blue sky research” because of the demand from policymakers or

stakeholders as well as from funding agencies worldwide. Maintaining balance in

this area would be very important. Therefore this book focuses on both aspects –

basic science, which is mostly curiosity driven, and applications such as the use of

and identification of biomarkers and glycan-based therapeutics in medical science.

The aim of this book is to provide a concise overview of the current status of

glycoscience in basic biology and medical applications including the mechanisms

of various diseases, biomarker discovery, and therapeutics and to propose future

directions in order to facilitate the further integration of glycoscience with other

areas of biology and medicine. This book addresses two salient points. First, it

provides readers with numerous simple overviews of current topics in the field

of glycoscience. Second, this book is not simply a series of reviews in the field of

vii

glycoscience but it is arranged is such a way that readers will have the opportunity

to become familiar with concepts of glycoscience and with the current protocols

used in experiments. The book is aimed at university students at graduate and

postdoctoral levels, professionals, and researchers including nonexperts in

glycobiology and glycochemistry.

The impetus for publishing this book arose from the Japan Consortium for

Glycobiology and Glycotechnology (JCGG). Many scientists who are consortium

members played pivotal roles in serving as authors, editors, and section editors.

Without their volunteer work, the publication of this book would not have been

possible. We had planned to publish the book in time for the joint meeting of the

Society for Glycobiology (SFG) and the Japanese Society of Carbohydrate

Research (JSCR) to be held on November 16–19, 2014, in Honolulu. This explains

the need to impose time constraints in terms of contributions. Fortunately most of

the scientists who were invited to contribute to the project gladly accepted our

request in spite of their busy schedules, and over 360 authors including coauthors

contributed in spite of the time constraints that we imposed on ourselves. Because

of their generosity and hard work, we were able to publish this book on time.

I would like to express our sincere thanks to all of the authors who contributed

to each chapter. We are particularly indebted to Ms. Fumi Ota at Systems

Glycobiology Research Group, RIKEN, who prepared a list of all authors who

submitted manuscripts and organized them on an online system as part of her busy

schedule as a member of the technical research staff. Finally, we are very grateful to

Ms. Aiko Hiraguchi and Mr. Kaoru Hashimoto of Springer Japan, who accepted our

original proposal. In addition, we are deeply grateful to Mr. Abhijit Baroi and

Ms. Swayamsiddha Das and the staff members at Springer who prepared the print

and online versions of this book for publication. Without their tremendous contri-

butions, the publication of this book would not have been possible.

August 2014 Naoyuki Taniguchi

Tamao Endo

Gerald W. Hart

Peter H. Seeberger

Chi-Huey Wong

viii Preface

About the Editors

Naoyuki Taniguchi graduated from the

Faculty of Medicine of Hokkaido University

at Sapporo, Japan. After internship, he entered

the Graduate School of Medicine and obtained

his MD degree in 1967 and then the PhD degree

in Biochemistry from the same university in

1972. He became Assistant Professor of the

Department of Preventive Medicine, Hokkaido

University, and visiting Associate Professor

at the Department of Biochemistry, Connell

University Medical School, New York in

1976. He became Assistant Professor of Cancer

Institute, Faculty of Medicine, Hokkaido

University. Between 1986 and 2006, Professor

Taniguchi served as Professor and Chair of the Department of Biochemistry, Osaka

University Medical School. In 2006 he became Professor Emeritus of Osaka

University, and after retirement from the medical school, he became an endowed

chair professor of Osaka University. Meanwhile, he launched Systems

Glycobiology Research Group at RIKEN in 2007, and since then he has been

leading this group as the Group Director. In 2011, he contributed to the initiation

of the RIKEN-Max Planck Joint Research Center at RIKEN. One of his partners of

the joint research center at MPI is Professor Peter Seeberger in Berlin, who is also

one of the Editors of this book.

Professor Taniguchi’s research focuses on the structure and function of glycans,

especially the role of branched N-linked glycoproteins in relation to the mechanism

of the disease biomarker discovery and therapeutics, especially for primary hepa-

toma, pancreatic cancer, chronic obstructive pulmonary disease (COPD), and

Alzheimer’s disease. His group essentially purified most N-glycan branching

enzymes such as GnT-III, IV, Va, and Fut 8 and also cloned all their genes

including GnT-IX (Vb). His group identified carrier proteins designated as target

molecules by lectin and mass spectrometry, and some of them are growth factor

receptors and adhesion molecules such as E-cadherin and integrins.

ix

Professor Taniguchi has received several distinguished awards such as IGO

(International Glycoconjugate Organization) Award in 2001, Medal with Purple

Ribbon from the Emperor of Japan in 2005, HUPO (Human Proteome Organiza-

tion) Distinguished Service Award in 2009, and Japan Academy Prize in 2011.

He served for 15 years as an editorial board member for Journal of BiologicalChemistry till 2013 and currently serves as an Editor of journals such as Biochem-ical and Biophysical Research Communications, Proteomics, Glycobiology,Glycoconjugate Journal, Protein Purification Expression and Purification, andCellular and Molecular Life Sciences. Professor Taniguchi has published more

than 400 original papers and more than 50 reviews. Recently he edited the second

edition of the bookHandbook of Glycosyltransferases and Related Genes publishedby Springer with more than 100 authors who are eminent in the field. He is also

President of Japan Consortium for Glycobiology and Glycotechnology (JCGG) and

Vice Director General of Sapporo Cancer Seminar Foundation. Furthermore, he

served as President of the 75th Annual Meeting of the Japanese Biochemical

Society in 2004, Secretary General of the 20th IUBMB 11FAOBMB Congress at

Kyoto, Japan, in 2006 and one of the Chairs of HUPO 12th Congress in 2013.

At present, Professor Taniguchi is the President of Society for Glycobiology

(SFG) in the USA and will organize the joint meeting of SFG and Japanese Society

of Carbohydrate Research as a Chair.

Tamao Endo graduated from the Faculty of

Pharmaceutical Sciences of the University of

Tokyo in 1977 and obtained his PhD at the

same institution in 1982 (under Professor

Shoshichi Nojima). He was a postdoctoral

fellow at the Baylor College of Medicine in

Houston (under Professor Donald M. Marcus)

and a research associate in the Institute of

Medical Science of the University of Tokyo

(under Professor Akira Kobata). Since 1994,

Dr. Endo has been the Head of Department of

Glycobiology, Tokyo Metropolitan Institute of

Gerontology (TMIG). He is now the Vice

Director of the Institute. His current research

interests are in the glycobiology of aging, dementia, and development. One of his

major research areas is understanding the molecular basis of the function of protein

O-mannosylation and its pathogenesis. His other areas of glycobiology research

include the development of methods of glycan analysis, disease-associated alter-

ation of protein glycosylation such as in diabetes and Alzheimer’s disease, and

launch of new glycobiology in the field of aging research.

Dr. Endo received several distinguished awards such as Tokyo Metropolitan

Governor’s Award in 2002, The Pharmaceutical Society of Japan Award for

Divisional Scientific Promotion in 2003, and The Asahi Award in 2007. He served

as an editorial board member for Biochimica et Biophysica Acta, The Journal of

x About the Editors

Biochemistry, and Biological and Pharmaceutical Bulletin and currently serves in

this capacity for Glycobiology and Journal of Histochemistry & Cytochemistry.He was the President of Japanese Society of Carbohydrate Research (JSCR) in

Japan, and is a Member of Science Council of Japan.

Gerald W. Hart is the Director and DeLamar

Professor of Biological Chemistry at Johns

Hopkins University School of Medicine. He

began his research on glycoconjugates about

40 years ago, and he has been active in the

field ever since. He did some of the very earliest

studies on cell surface heparan sulfate proteo-

glycans (e.g., Developmental Biol. (1975) 44,253). He characterized the roles of glycosami-

noglycans and hyaluronic acids in the develop-

ment of corneal transparency and performed

early studies on the importance of proteoglycan

sulfotransferases (e.g., J. Biol. Chem. (1976)251, 6513; J. Biol. Chem. (1978) 253, 347).

He showed that keratan sulfate I is synthesized by the N-linked biosynthetic

pathway, and he established that the sequon Asn-X-Ser(Thr) is the minimal struc-

tural requirement for N-glycan oligosaccharyltransferase to attach N-glycans to

proteins.

Professor Hart’s laboratory performed some of the earliest studies mapping

N-glycan attachment sites, and they were among the first to show that N-linked

protein glycosylation heterogeneity is site specific and highly regulated by cellular

physiology (e.g., J. Biol. Chem. (1985) 260, 4046). They also showed that site-

specific N-linked glycosylation is tightly controlled also by protein structure at all

levels (e.g., J. Biol. Chem. (1986) 261, 13186–13196). The Hart laboratory purifiedseveral of the most important glycosyltransferases and developed methods to use

them to probe glycan structures on living cells (e.g., Meth. Enzymol. (1989)

179, 82). In collaboration with Paul Englund’s group at Johns Hopkins, they

elucidated the biosynthetic pathway for GPI-Anchors (e.g., Cell (1989) 56, 793).In the early 1980s while probing cells with glycosyltransferases, the Hart laboratory

discovered cytoplasmic and nuclear protein glycosylation by O-linked N-acetylglu-cosamine (O-GlcNAc) (e.g., J. Biol. Chem. 259, 3308; J. Biol. Chem. 261, 8049).Since that time, the Hart laboratory has published over 200 papers on

O-GlcNAcylation identifying and cloning the enzymes controlling cycling, char-

acterizing O-GlcNAcylation and its interplay with phosphorylation on hundreds of

proteins, and they have developed many of the tools and methods in use today to

study this modification.

In 1989, Professor Hart founded the leading journal in the field, Glycobiology,serving as Editor-In-Chief until 2001. He received the first International

Glycoconjuate Organization (IGO) Award in 1997 and the Karl Meyer Award

from the Society for Glycobiology in 2006 and served as the 2009–2011 president

About the Editors xi

of the IGO. He is currently an Associate Editor for The Journal of BiologicalChemistry and an Associate Editor forMolecular and Cellular Proteomics. Currentareas of research focus are the regulation of kinases by O-GlcNAcylation, defining

the O-GlcNAcome of the mitochondria, and elucidating the O-GlcNAc Regulation

of Mitochondrial Functions and O-GlcNAc Regulation of Transcription. To date,

Professor Hart has published about 274 papers, all in the area of glycosciences

(Google Scholar H-factor ¼ 97; i10-index¼246).

Peter H. Seeberger studied chemistry and

biochemistry in Erlangen (Germany) and

Boulder (USA). After completing his PhD and

carrying out research at the Sloan-Kettering

Cancer Research Center in New York, he built

an independent research program at MIT where

he was promoted to Firmenich Associate

Professor of Chemistry with tenure after just

4 years. After 6 years as Professor at the Swiss

Federal Institute of Technology (ETH) Zurich,

he assumed positions as Director at the Max

Planck Institute for Colloids and Interfaces in

Potsdam (Germany) and Professor at the Free

University of Berlin. In addition he serves as

Affiliate Professor at the Sanford-Burnham Institute for Medical Research

(La Jolla, USA) and Honorary Professor at the University of Potsdam.

Professor Seeberger’s research on the chemistry and biology of carbohydrates,

continuous flow chemistry and automation of chemistry, carbohydrate vaccine

development and a broad range of topics from engineering to immunology has

been documented in over 360 peer-reviewed journal articles, two books, more than

30 patents, over 150 published abstracts and more than 630 invited lectures. This

work was recognized with more than 25 international awards from the USA

(including the Arthur C. Cope Young Scholar Award, Horace B. Isbell Award,

and Claude S. Hudson Award from the American Chemical Society), Germany

(including the Korber Prize for European Sciences), Holland (Havinga Medal),

Israel (Honorary Lifetime Member of the Israel Chemical Society), Japan

(Yoshimasa Hirata Gold Medal), Switzerland (“The 100 Most Important Swiss”),

and international organizations (Whistler Award 2012 of the International Carbo-

hydrate Society). In 2013 he was elected to the Berlin-Brandenburg Academy of

Sciences. The research carried out at the Seeberger laboratory has given rise to

several spin-off companies in the USA and Germany.

Professor Seeberger has served the scientific community in many functions.

He greatly supports the idea of open access publishing as the Editor-in-Chief of the

Beilstein Journal of Organic Chemistry. He was the Editor of the Journal ofCarbohydrate Chemistry and serves on the editorial advisory boards of many

other journals.

xii About the Editors

Through his work in the area of neglected diseases, Professor Seeberger has been

involved in philanthropic causes. He is a cofounder of the Tesfa-Ilg “Hope for

Africa” Foundation, which aims at improving health care in Ethiopia. The Founda-

tion recently helped to build a bednet factory and established an IT training center.

Chi-Huey Wong received his BS (1970) and

MS (1977) degrees from National Taiwan

University and PhD (1982) in Chemistry (with

George M. Whitesides) from Massachusetts

Institute of Technology. He then worked at

Harvard University as a postdoctoral fellow

(with George M. Whitesides) for another year

and became a faculty member at Texas A&M

University (1983), where he was promoted to

full professor in 1987. He then moved to the

Scripps Research Institute in 1989 as Professor

and Ernest W. Hahn Chair in Chemistry until

2006. From 2003 to 2006, he also served as

Director of the Genomics Research Center at

Academia Sinica, Taipei and since October 2006, he has been President of

Academia Sinica with a joint appointment as Professor of Chemistry at the Scripps

Research Institute and National Taiwan University.

Professor Wong is a recipient of The Searle Scholar Award in Biomedical

Sciences (1985), the Presidential Young Investigator Award in Chemistry, USA

(1986), the American Chemical Society A. C. Cope Scholar Award (1993), the Roy

Whistler Award of the International Carbohydrate Organization (1994), the Amer-

ican Chemical Society Harrison Howe Award in Chemistry (1998), the American

Chemical Society Claude S. Hudson Award in Carbohydrate Chemistry (1999), the

International Enzyme Engineering Award (1999), the US Presidential Green Chem-

istry Challenge Award (2000), the American Chemical Society Award for Creative

Work in Synthetic Organic Chemistry (2005), the Humboldt Research Award for

Senior Scientists (2006), the FA Cotton Medal (2008), the Nikkei Asia Prize for

Science, Technology and Innovation (2012), the American Chemical Society

Arthur C. Cope Award (2012), and the Wolf Prize in Chemistry (2014).

Professor Wong is a member of Academia Sinica (1994), the American Acad-

emy of Arts and Sciences (1996), the US National Academy of Sciences (2002),

and the World Academy of Sciences (2007). He served as an Editorial Advisory

Board member for the Journal of American Chemical Society and AngewandteChemie, Chairman of the Executive Board of Editors of the Tetrahedron Publica-

tions (2006–2008), Head of the Frontier Research Program on Glycotechnology at

RIKEN in Japan (1991–1999), and a board member of the US National Research

Council on Chemical Sciences and Technology (2000–2003). In addition, he has

received many honorary doctorate degrees and served as science advisor to many

organizations including as scientific advisor to the Max Planck Institute

(2000–2008), advisory council member of RIKEN (2010 till date), member of the

About the Editors xiii

Board of Scientific Governors of the Scripps Research Institute (2009 till date) and

the Chief Science Advisor of the Taiwan Government (2008 till date).

Professor Wong’s research interests are in the field of chemical biology with

particular focus on the development of new methods for the synthesis of complex

carbohydrates and glycoproteins, elucidation of carbohydrate-mediated biological

recognition associated with protein folding, cancer progression and bacterial or

viral infection, and development of carbohydrate-based vaccines, therapeutics, and

devices. He has published over 700 papers and holds 100 patents and is a highly

cited scientist with H-index ¼ 100.

xiv About the Editors

Section Editors

Takashi Angata Institute of Biological Chemistry, Academia Sinica, NanKang,

Taipei, Taiwan

Kiyoko F. Aoki-Kinoshita Department of Bioinformatics, Faculty of Engineer-

ing, Soka University, Tokyo, Japan

xv

Tamao Endo Tokyo Metropolitan Institute of Gerontology, Tokyo Metropolitan

Geriatric Hospital and Institute of Gerontology, Tokyo, Japan

Jin-ichi Inokuchi Division of Glycopathology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai,

Miyagi, Japan

xvi Section Editors

Kenji Kadomatsu Graduate School of Medicine, Nagoya University, Nagoya,

Japan

Yasuhiro Kajihara Department of Chemistry, Osaka University, Osaka, Japan

Section Editors xvii

Ken Kitajima Bioscience and Biotechnology Center, Nagoya University,

Chikusa, Nagoya, Japan

Shoko Nishihara Department of Bioinformatics, Faculty of Engineering, Soka

University, Tokyo, Japan

xviii Section Editors

Naoyuki Taniguchi Systems Glycobiology Research Group, RIKEN-Max Planck

Joint Research Center for Systems Chemical Biology, Global Research Cluster,

RIKEN, Saitama, Japan

Osaka University, Osaka, Japan

Chi-Huey Wong Academia Sinica, NanKang, Taipei, Taiwan

The Scripps Research Institute, La Jolla, CA, USA

Section Editors xix

Yoshiki Yamaguchi Structural Glycobiology Team, Systems Glycobiology

Research Group, RIKEN-Max Planck Joint Research Center, RIKEN Global

Research Cluster, Saitama, Japan

xx Section Editors

Contents

Volume 1

Part I Introduction to Glycoscience . . . . . . . . . . . . . . . . . . . . . . . . . 1

1 Glycoscience: Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

Richard D. Cummings

2 Current Status and New Challenges in

Glycoscience: Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11

Chi-Huey Wong and Naoyuki Taniguchi

Part II Analytical and Structural Approach: Technical Descriptionfor Analyzing Glycans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15

3 EMARS Method: Tool for Molecular Interactome . . . . . . . . . . . 17

Koichi Honke and Norihiro Kotani

4 Neoglycolipid (NGL)-Based Glycan Microarray System for

Ligand Discovery . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25

Yan Liu, Robert A. Childs, and Ten Feizi

5 Preparation of Glycan Array and Its Applications . . . . . . . . . . . 35

Chung-Yi Wu and Chi-Huey Wong

6 Automated Programmable One-Pot Synthesis of Glycans . . . . . 45

Chung-Yi Wu and Chi-Huey Wong

7 Historical and Practical Aspects of Development of Lectin

Microarray Technique . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53

Jun Hirabayashi

8 Mining and Using Glycan Array Data with the GlycoSearch

Analysis Program and GlycanBinder Database . . . . . . . . . . . . . . 61

Doron Kletter, Marshall Bern, and Brian Haab

9 Mass Spectrometric Analyses of Cell and Tissue Glycomes . . . . 69

Stuart M. Haslam, Poh-Choo Pang, Aristotelis Antonopoulos, and

Anne Dell

xxi

10 Mass Spectrometry-Based Protein Glycosylation Analysis from

Sulfoglycomics to Glycoproteomics . . . . . . . . . . . . . . . . . . . . . . . 79

Kay-Hooi Khoo

11 Methods for Large-Scale Glycosylation Site Mapping of

N-Glycoproteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87

Hiroyuki Kaji

12 Supported Molecular Matrix Electrophoresis . . . . . . . . . . . . . . . 95

Akihiko Kameyama and Yu-ki Matsuno

13 Simultaneous Quantification of Nucleotide Sugar Metabolism

by LC and LC-MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 103

Kazuki Nakajima and Naoyuki Taniguchi

14 Capillary Electrophoresis of Glycans: Validation of Antibody

Pharmaceuticals Based on Glycan Profiles . . . . . . . . . . . . . . . . . 111

Mitsuhiro Kinoshita and Kazuaki Kakehi

15 Congenital Disorders of Glycosylation, Analytical Aspects . . . . . 119

Yoshinao Wada

16 Indirect Detection of Hydroxy Proton Exchange Through

Deuterium-Induced 13C-NMR Isotope Shifts . . . . . . . . . . . . . . . . 129

Shinya Hanashima and Yoshiki Yamaguchi

17 Paramagnetism-Assisted Nuclear Magnetic Resonance Analysis

of Dynamic Conformations and Interactions of

Oligosaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137

Takumi Yamaguchi and Koichi Kato

18 Glycosphingolipid Analysis by Liquid Chromatography-Mass

Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147

Akemi Suzuki, Kunihiro Sano, Minoru Suzuki,

Yoshikatsu Umemura, and Hideshi Fujiwake

19 Analysis of Sulfoglycolipids by Mass Spectrometry . . . . . . . . . . . 155

Michael Tiemeyer and Kazuhiro Aoki

20 Conventional and Easy Analysis of Virus-Binding

GAG Structure Using Array-Type Sugar Chip . . . . . . . . . . . . . . 163

Yasuo Suda, Xu Zhang, Sachiko Nakamura-Tsuruta, Michael Sobel,

Toshiomi Okuno, and Masahiro Wakao

21 X-Ray Crystallography of Sugar Related Proteins . . . . . . . . . . . 175

Hisayoshi Makyio and Ryuichi Kato

xxii Contents

Part III Glycoinformatics: New Approach for Informatics andDatabases for Glycoscience . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183

22 Glycoinformatics: Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185

Kiyoko F. Aoki-Kinoshita

23 Minimum Information Required for a Glycomics Experiment

(MIRAGE): Enhancing the Value of Glycoanalytic Data . . . . . . 193

Daniel Kolarich, Rene Ranzinger, Carsten Kettner, and

William S. York

24 RINGS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 201

Kiyoko F. Aoki-Kinoshita

25 JCGGDB . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209

Toshihide Shikanai and Hisashi Narimatsu

26 UniCarbKB: Emergent Knowledgebase for Glycomics . . . . . . . . 215

Matthew P. Campbell, Robyn Peterson, Elisabeth Gasteiger,

Julien Mariethoz, Frederique Lisacek, and Nicolle H. Packer

27 Systematic and Quantitative Identification of Cellular Glycan

Regulation Using Correlation Index-Based Responsible

Gene Screening (CIRES) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223

Hiromu Takematsu

28 Databases and Tools of GLYCOSCIENCES.de Web Server . . . 233

Miguel A. Rojas-Macias, Alexander Loss, Andreas Bohne-Lang,

Martin Frank, and Thomas L€utteke

29 Bacterial, Plant, and Fungal Carbohydrate Structure

Database (CSDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241

Philip Toukach and Ksenia Egorova

30 Problems and Pitfalls of Residue Notation in Glycoinformatics . . . 251

Thomas L€utteke

31 GlycomeDB . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 259

Rene Ranzinger and William S. York

32 GlycoEpitope: Database for Carbohydrate

Antigen and Antibody . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 267

Shujiro Okuda, Hiromi Nakao, and Toshisuke Kawasaki

33 SugarBindDB: Resource of Pathogen Lectin-Glycan

Interactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275

Julien Mariethoz, Khaled Khatib, Matthew P. Campbell,

Nicolle H. Packer, Elaine Mullen, and Frederique Lisacek

34 3D-Lectin Database . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 283

Serge Perez, Alain Rivet, and Anne Imberty

Contents xxiii

Part IV Chemoenzymatic Synthesis of Glycans: Chemical andEnzymatic Methods of Glycan Synthesis . . . . . . . . . . . . . . . . . . . . . 291

35 Chemoenzymatic Synthesis of Glycans: Overview . . . . . . . . . . . . 293

Chi-Huey Wong

36 Acid-Base Catalysis Concept in Glycosidation . . . . . . . . . . . . . . . 295

Amit Kumar and Richard R. Schmidt

37 Synthetic Approach to Glycoprotein Quality Control System . . . 305

Yukishige Ito, Akira Seko, and Yoichi Takeda

38 Chemical Synthesis of Homogeneous Glycoproteins . . . . . . . . . . 313

Masayuki Izumi, Ryo Okamoto, and Yasuhiro Kajihara

39 Glycopeptide/Glycoprotein Synthesis . . . . . . . . . . . . . . . . . . . . . . 323

Ci Xu and Xuechen Li

40 Gangliosides Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 331

Makoto Kiso, Hideharu Ishida, Hiromune Ando, and Akihiro Imamura

41 Glycosylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 339

David Crich

42 Automation in Glycan Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . 345

Chung-Yi Wu and Chi-Huey Wong

43 Chemical Synthesis of Oligosialic Acid Using 5-N,4-O-CarbonylProtected Sialyl Donors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353

Hiroshi Tanaka

44 Synthesis of 1,2-cis Amino Glycoside . . . . . . . . . . . . . . . . . . . . . . 359

Shino Manabe

45 Synthesis of Sulfated Glycans . . . . . . . . . . . . . . . . . . . . . . . . . . . . 365

Medel Manuel L. Zulueta and Shang-Cheng Hung

46 Synthetic Carbohydrate Antigens for HIV Vaccine Design . . . . . 373

Lai-Xi Wang

47 Glycoenzymes in Glycan Analysis and Synthesis . . . . . . . . . . . . . 379

Toshihiko Katoh and Kenji Yamamoto

48 Endo-enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 391

Kenji Yamamoto

49 Sugar Oxazolines as Directly Preparable Glycosyl Donors from

Unprotected N-Acetyl-2-Amino Sugars: Towards One-Pot

Chemo-Enzymatic Synthesis of Glycoproteins Catalyzed by

N-Acetylglucosaminidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 401

Shin-ichiro Shoda, Atsushi Kobayashi, and Masato Noguchi

xxiv Contents

50 Large-Scale Enzymatic Synthesis of Glycans with Cofactor

Regeneration . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 409

Tsung-I Tsai, Chung-Yi Wu, and Chi-Huey Wong

51 Chemoenzymatic Synthesis of Heparins . . . . . . . . . . . . . . . . . . . . 419

Demetria M. Dickinson, Jian Liu, and Robert J. Linhardt

52 Chemoenzymatic Synthesis of Glycoproteins . . . . . . . . . . . . . . . . 427

Guohui Zhao, Yunpeng Liu, Zhigang Wu, Hailiang Zhu,

Zaikuan Yu, Junqiang Fang, and Peng George Wang

53 Structural Biology of Oligosaccharyltransferase (OST) . . . . . . . 437

Shunsuke Matsumoto, James Nyirenda, and Daisuke Kohda

54 Synthesis of O-Glycoprotein . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 447

Hironobu Hojo

Part V Imaging of Glycans: New Techniques . . . . . . . . . . . . . . . . . 453

55 Molecular Probes for Glycosylation: Overview . . . . . . . . . . . . . . 455

Chi-Huey Wong

56 Imaging by Click Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 459

Chung-Yi Wu and Chi-Hui Wong

57 Imaging Cell Surface Glycans in Animals with Bioorthogonal

Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 467

Brendan J. Beahm and Carolyn R. Bertozzi

58 Chemical Tools to Detect and Target Helicobacter pylori’sGlycoproteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 479

Van N. Tra and Danielle H. Dube

59 PET Imaging of Glycoconjugates . . . . . . . . . . . . . . . . . . . . . . . . . 485

Katsunori Tanaka

60 Glycoform Imaging . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 491

Yoshimi Haga and Tadashi Suzuki

Part VI Neuroglycobiology: Role of Glycans in Neurobiology andNeuroscience . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 495

61 Glycoconjugate Antigens in Neural Stem Cells . . . . . . . . . . . . . . 497

Yutaka Itokazu and Robert K. Yu

62 Glycosaminoglycans: Key Regulator for Recovery from

Neuronal Injuries . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 505

Kenji Kadomatsu

63 Glycosaminoglycans: Modes of Action for Possible New Avenue

for Therapeutic Intervention . . . . . . . . . . . . . . . . . . . . . . . . . . . . 511

Tadahisa Mikami and Hiroshi Kitagawa

Contents xxv

64 Polysialic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 519

Chihiro Sato and Ken Kitajima

65 Polysialyltransferase Assay . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 529

Masaya Hane, Ken Kitajima, and Chihiro Sato

66 Gangliosides in Axon Stability and Regeneration . . . . . . . . . . . . 535

Ronald L. Schnaar

67 HNK-1 Glyco-epitope: COMPLEX Machinery for

Biosynthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 543

Naoki Nakagawa and Shogo Oka

68 Gangliosides: Synthesis and Function in Nervous Tissues . . . . . . 551

Koichi Furukawa, Yuhsuke Ohmi, Yuki Ohkawa, Noboru Hashimoto,

Yoshio Yamauchi, Orie Tajima, and Keiko Furukawa

69 Single Molecule Imaging . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 557

Kenichi G. N. Suzuki

70 Profiling of Glucosylceramides by Liquid

Chromatography-Tandem Mass Spectrometry . . . . . . . . . . . . . . 565

Kazuki Nakajima, Ayako Kohyama-Koganeya, and

Yoshio Hirabayashi

71 Heparan Sulfate Proteoglycans in Central Synapses . . . . . . . . . . 573

Yu Yamaguchi and Fumitoshi Irie

72 Heparan Sulfate Proteoglycans in Drosophila melanogaster . . . . 581

Keisuke Kamimura and Nobuaki Maeda

73 N-Glycans and Glial Cells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 589

Kazuhiro Ikenaka

Part VII Immunoglycobiology: Role of Glycans inImmunoreactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 595

74 Immunoglycobiology: Overview . . . . . . . . . . . . . . . . . . . . . . . . . . 597

Ada G. Blidner, Juan M. Ilarregui, and Gabriel A. Rabinovich

75 Siglecs and B Cell Regulation . . . . . . . . . . . . . . . . . . . . . . . . . . . . 609

Takeshi Tsubata

76 Sialyl Sulfoglycans in Immune Regulation and Their Clinical

Applications . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 617

Reiji Kannagi, Keiichiro Sakuma, and Katsuyuki Ohmori

77 Glycosylation in High Endothelial Venules . . . . . . . . . . . . . . . . . 627

Hiroto Kawashima

78 Siglec Interactions with Pathogens . . . . . . . . . . . . . . . . . . . . . . . . 633

Takashi Angata and Ajit Varki

xxvi Contents

79 Major Histocompatibility Complex: N-Glycosylation Form

and Function . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 643

Sean O. Ryan and Brian A. Cobb

80 DC-SIGN. C-Type Lectin with Prominent Role in

Immune System . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 649

Juan J. Garcia-Vallejo and Yvette van Kooyk

81 Glycosylation Density in Cellular Homeostasis . . . . . . . . . . . . . . 661

C. Fred Brewer

82 Gangliosides in T Cell Immunity . . . . . . . . . . . . . . . . . . . . . . . . . 667

Masakazu Nagafuku and Jin-ichi Inokuchi

83 C-Type Lectins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 675

Timo Johannssen, Julia H€utter, Stephanie Zimmermann, and

Bernd Lepenies

84 Microbial Glycoconjugates Recognition with TLRs and

NLRs in Innate Immunity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 685

Yukari Fujimoto and Koichi Fukase

85 Polylactosamine and Immunity . . . . . . . . . . . . . . . . . . . . . . . . . . 691

Akira Togayachi

86 Glycosphingolipid-Receptor Interactions in the Innate Immune

Response . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 699

Hitoshi Nakayama and Kazuhisa Iwabuchi

87 Toll Like Receptors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 707

Natsuko Tanimura and Kensuke Miyake

88 Mucin-Type O-Glycan in Megakaryocyte Differentiation . . . . . . 713

Takashi Kudo and Satoru Takahashi

Part VIII Microbial Glycobiology and Infection Glycobiology:Role of Glycans in Infections . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 721

89 Helicobacter pylori . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 723

Masatomo Kawakubo, Yuki Ito, Minoru Fukuda, and Jun Nakayama

90 Norovirus and Histo-Blood Group Antigens . . . . . . . . . . . . . . . . 731

Haruko Shirato

91 Peptidoglycan and Nod Receptor . . . . . . . . . . . . . . . . . . . . . . . . . 737

Richard Wheeler, Frederic Veyrier, Catherine Werts, and

Ivo Gomperts Boneca

92 Influenza Virus, Overview: Structures, Infection Mechanisms

and Antivirals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 749

Raphael Bohm, Thomas Haselhorst, and Mark von Itzstein

Contents xxvii

93 Binding of Influenza Viruses to Glycans . . . . . . . . . . . . . . . . . . . 769

Tadanobu Takahashi and Takashi Suzuki

94 HIV and Galectins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 775

Michel Ouellet, Michel J. Tremblay, and Sachiko Sato

95 Viral Interactions with Glycans . . . . . . . . . . . . . . . . . . . . . . . . . . 785

Tadahiro Suenaga and Hisashi Arase

96 Comparative Glycobiology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 795

Katharina Paschinger and Iain B. H. Wilson

Volume 2

Part IX Developmental Glycobiology . . . . . . . . . . . . . . . . . . . . . . . 807

97 O-Linked Glycans in Drosophila Development: Overview . . . . . 809

Amanda R. Haltom and Hamed Jafar-Nejad

98 Glycosaminoglycans and Glycosylphosphatidylinositol-Anchor

Proteins in Development of Caenorhabditis elegans . . . . . . . . . . . 817

Kazuya Nomura, Sayaka Akiyoshi, Ayako Matsuda, and

Kazuko H. Nomura

99 Heparan Sulfate Proteoglycans in Drosophila Ovarian Germline

Stem Cell Niche . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 825

Hiroshi Nakato

100 O-Glycosylation in Development of Zebrafish . . . . . . . . . . . . . . . 833

Akira Kurosaka, Yoshiaki Nakayama, and Naosuke Nakamura

101 O-Fucose Glycan in Drosophila Notch Signaling . . . . . . . . . . . . . 841

Kenjiroo Matsumoto, Akira Ishio, and Kenji Matsuno

102 O-Glucose Glycans in Drosophila Notch Signaling . . . . . . . . . . . 849

Tom V. Lee and Hamed Jafar-Nejad

103 O-Glycans in Mammalian Notch Signaling . . . . . . . . . . . . . . . . . 857

Pamela Stanley

104 Carbohydrate-Based Gamete Recognition During the Sperm

Acrosome Reaction in Sea Urchins . . . . . . . . . . . . . . . . . . . . . . . . 865

Noritaka Hirohashi

105 Sulfated Polysaccharide-Dependent Activation of Sperm in

Sea Urchin Fertilization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 875

Ana Cristina E. S. Vilela-Silva, V. H. Pomin, and P. A. S. Mourao

xxviii Contents

106 Flagellasialin: Highly Glycosylated GPI-Anchored Protein

Involved in Intracellular Ca2+ Regulation in Sea

Urchin Sperm . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 883

Takeru Kanazawa, Eriko Suzuki, Shinji Miyata, Chihiro Sato, and

Ken Kitajima

107 Functional Analysis of Glycans Using Drosophila Mutants

and RNAi . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 891

Takashi J. Fuwa and Shoko Nishihara

Part X Glycan Recognition, Quality Control and Metabolism:Role of Glycan Recognition on Cell Surface, Cytosol andMetabolic Pathway . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 901

108 Quality Control System for Glycoproteins in Endoplasmic

Reticulum: Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 903

Tadashi Suzuki

109 Free Oligosaccharides (High Mannose-Type Free Glycans

Found in Mammals and Yeast) . . . . . . . . . . . . . . . . . . . . . . . . . . 907

Tadashi Suzuki

110 UDP-Glucose: Glycoprotein Glucosyltransferase in ER

Glycoprotein Quality Control . . . . . . . . . . . . . . . . . . . . . . . . . . . . 913

Cecilia D’Alessio and Armando J. Parodi

111 pH Control in Golgi Apparatus and Congenital Disorders

of Glycosylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 921

Yusuke Maeda

112 Generating Isoform-Specific Antibodies: Lessons from

Nucleocytoplasmic Glycoprotein Skp1 . . . . . . . . . . . . . . . . . . . . . 927

Christopher M. West, Hanke van der Wel, Zoiesha Chinoy,

Geert-Jan Boons, Ted J. Gauthier, Carol M. Taylor, and Yuechi Xu

113 Intracellular Lectin, ERGIC 53 . . . . . . . . . . . . . . . . . . . . . . . . . . 935

Kazuo Yamamoto

114 Retrograde Membrane Traffic and Recycling Endosome . . . . . . 943

Yuichi Takeda and Tomohiko Taguchi

115 Localization of Glycosylenzymes and Nucleotide-Sugar

Transporters in Endoplasmic Reticulum and Golgi

Apparatus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 949

Miki Yamamoto-Hino and Satoshi Goto

116 Traffic of Botulinum Toxin Complex: Crystal Structure and

Role of Toxin Complex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 955

Takashi Tonozuka, Keiji Oguma, and Atsushi Nishikawa

Contents xxix

117 Homogeneous Glycoproteins: Overview . . . . . . . . . . . . . . . . . . . 959

Chi-Huey Wong

118 N-Glycan Branching and Its Biological Significance . . . . . . . . . . 963

Naoyuki Taniguchi and Yasuhiko Kizuka

119 Integrin α5β1 and Its N-Glycosylation . . . . . . . . . . . . . . . . . . . . . 971

Jianguo Gu, Qinglei Hang, Tomohiko Fukuda, and Tomoya Isaji

120 E-Cadherin Glycosylation in Cancer . . . . . . . . . . . . . . . . . . . . . . 977

Salome S. Pinho and Celso A. Reis

121 Functional Regulation of ErbB Receptors by N-Glycans . . . . . . 983

Motoko Takahashi

122 Core Fucosylation of N-Linked Glycan for Fine-Tuning

TGF β Receptor Function . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 991

Xiangchun Wang and Naoyuki Taniguchi

123 FGF System and GAGs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 999

Toru Imamura

124 GLUTII . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1007

Kazuaki Ohtsubo

125 C-Type Lectin Family: Overview . . . . . . . . . . . . . . . . . . . . . . . . 1015

Maureen E. Taylor and Kurt Drickamer

126 Mannan-Binding Protein (MBP)-Ligand Glycans:

Novel Tissue Marker for Colorectal Carcinomas . . . . . . . . . . . . 1021

Toshisuke Kawasaki, Motohiro Nonaka, and Nobuko Kawasaki

127 New Aspects of Collectin Functions . . . . . . . . . . . . . . . . . . . . . . . 1029

Katsuki Ohtani, Yasuhiko Suzuki, and Nobutaka Wakamiya

128 Mannose 6-Phosphate Receptors . . . . . . . . . . . . . . . . . . . . . . . . . 1037

Linda J. Olson and Nancy M. Dahms

129 Protein O-GalNAc Glycosylation: Most Complex and

Differentially Regulated PTM . . . . . . . . . . . . . . . . . . . . . . . . . . . 1049

Hiren J. Joshi, Catharina Steentoft, Katrine T.-B. G. Schjoldager,

Sergey Y. Vakhrushev, Hans H. Wandall, and Henrik Clausen

130 O-Glycosylation and Development . . . . . . . . . . . . . . . . . . . . . . . . 1065

Kelly G. Ten Hagen

131 Biological Functions of C1GalT1 and Mucin-Type

O-Glycans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1073

Kirk Bergstrom, Jianxin Fu, and Lijun Xia

xxx Contents

132 Identification of Mammalian O-Mannosylated

Glycopeptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1081

Patrick R. Winterhalter, Thomas Ruppert, and Sabine Strahl

133 C-Mannosylation: Modification on Tryptophan in

Cellular Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1091

Yoshito Ihara, Yoko Inai, Midori Ikezaki, In-Sook L. Matsui,

Shino Manabe, and Yukishige Ito

134 Glc Transporter Assay and the New Intestinal Glycobiology . . . 1101

Kimie Asanuma-Date and Haruko Ogawa

135 Plant N-Glycans and Their Degrading Enzymes . . . . . . . . . . . . . 1111

Takeshi Ishimizu

136 Metabolism of Natural and Unnatural Sialic Acid . . . . . . . . . . . 1119

Akiko Fujita and Jennifer J. Kohler

Part XI Glycan Signaling and Regulation: Role of SignalingPathway and Gene Regulation of Glycan Synthesis . . . . . . . . . . . . 1127

137 Epigenetic Regulation of and by Glycosylation . . . . . . . . . . . . . . 1129

Yasuhiko Kizuka

138 Expression and Transcriptional Regulation of

β4-Galactosyltransferase Genes in Cancer . . . . . . . . . . . . . . . . . . 1135

Takeshi Sato and Kiyoshi Furukawa

139 β1,4-Galactosyltransferase: Regulation and Signaling

in Cancers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1141

Lei Zhou, Jianhai Jiang, and Jianxin Gu

140 ENPP3-Mediated Regulation of Glycan Biosynthesis . . . . . . . . . 1149

Hiroaki Korekane, Jong Yi Park, and Naoyuki Taniguchi

141 GM3 Synthase (ST3Gal5) and Diabetes . . . . . . . . . . . . . . . . . . . . 1157

Jin-ichi Inokuchi

142 Control of Glycans by Enzyme Competitions . . . . . . . . . . . . . . . 1163

Takahiro Okada, Hideyuki Ihara, and Yoshitaka Ikeda

143 Transcriptional Regulation of Glycan Expression . . . . . . . . . . . . 1173

Huabei Guo and J. Michael Pierce

144 Glycolipid Raft . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1181

Kazuya Kabayama, Hisao Kojima, and Yusuke Suzuki

145 Raft Signaling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1185

Kohji Kasahara

Contents xxxi

Part XII O-GlcNAcylation: Central Role of O-GlcNAc inMetabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1191

146 O-GlcNAcylation: Nutrient Sensor that Regulates

Cell Physiology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1193

Gerald W. Hart

147 O-GlcNAcylation: Nutrient Sensor in Chronic

Diseases of Aging . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1201

Gerald W. Hart

148 Diabetes and O-GlcNAcylation . . . . . . . . . . . . . . . . . . . . . . . . . . . 1207

Yoshihiro Akimoto, Yuri Miura, Tamao Endo,

Hayato Kawakami, and Gerald W. Hart

149 Functional Roles of O-GlcNAc in Cell Signaling . . . . . . . . . . . . . 1213

Sujin Park and Jin Won Cho

150 Extracellular O-GlcNAcylation . . . . . . . . . . . . . . . . . . . . . . . . . . 1221

Mitsutaka Ogawa, Koichi Furukawa, and Tetsuya Okajima

Part XIII Disease Glycomics and Glyco-Biomarkers: Implicationof Glycans in Disease and Application for Biomarkers . . . . . . . . . . 1227

151 Congenital Disorders of Glycosylation:

Glycosylphosphatidylinositol (GPI)-Related . . . . . . . . . . . . . . . . 1229

Yoshiko Murakami and Taroh Kinoshita

152 α-Dystroglycanopathy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1237

Tamao Endo

153 Dystroglycan: Extracellular Matrix Receptor that Links to

Cytoskeleton . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1245

Yuji Hara and Kevin P. Campbell

154 Members of the Nucleotide-Sugar Transporter Family and

Their Functions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1253

Shoko Nishihara

155 Chronic Obstructive Pulmonary Disease (COPD) . . . . . . . . . . . . 1267

Congxiao Gao and Naoyuki Taniguchi

156 Glycoredox: New Paradigm for Glycosylation and

Redox Signaling Research . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1275

Rina Takamiya, Kazuaki Ohtsubo, and Naoyuki Taniguchi

157 Glycosylation of Amyloid β Precursor Protein . . . . . . . . . . . . . . 1283

Shinobu Kitazume

xxxii Contents

158 Glycan Marker for Idiopathic Normal Pressure

Hydrocephalus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1289

Kyoka Hoshi, Yuka Matsumoto, Toshie Saito, Hiromi Ito,

Yoshinobu Kariya, Yoshiki Yamaguchi, Katsutoshi Furukawa,

Hiroyuki Arai, Masakazu Miyajima, Hajime Arai, Hisashi Narimatsu,

Kiyoshi Saito, Takashi Honda, and Yasuhiro Hashimoto

159 Rheumatoid Arthritis and IgG as Biomarker . . . . . . . . . . . . . . . 1297

Shiro Ohshima

160 Complex Genetics of Protein N-Glycosylation . . . . . . . . . . . . . . . 1303

Jasminka Kristic, Vlatka Zoldos, and Gordan Lauc

161 Metabolism of N-Glycolylneuraminic Acid in Human and

Nonhuman Cells, and Potential Relationships to

Human Disease . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1311

Anne K. Bergfeld, Annie N. Samraj, and Ajit Varki

162 C-Type Lectin Receptors in Host Defense Against Microbial

Pathogens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1319

Rikio Yabe, Yoichiro Iwakura, and Shinobu Saijo

163 Chondroitin Sulfate in Cartilage . . . . . . . . . . . . . . . . . . . . . . . . . 1331

Hideto Watanabe

164 Glycation of Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1339

Motoko Takahashi

Part XIV Role of Glycans in Cancer . . . . . . . . . . . . . . . . . . . . . . . . . 1347

165 Glycosylation in Cancer: Enzymatic Basis for Alterations in

N-Glycan Branching . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1349

Hiroaki Korekane and Naoyuki Taniguchi

166 Free Complex-Type N-Glycans . . . . . . . . . . . . . . . . . . . . . . . . . . 1357

Yasuhide Miyamoto

167 Hepatosteatosis and Primary Hepatoma . . . . . . . . . . . . . . . . . . . 1365

Eiji Miyoshi and Yoshihiro Kamada

168 Quantification of Prostate Cancer-Associated Aberrant

Glycosylation of Prostate-Specific Antigen . . . . . . . . . . . . . . . . . . 1373

Chikara Ohyama, Takuya Koie, Tohru Yoneyama, and

Yuki Tobisawa

169 Development and Actualization of Glycobiomarker Based

on the Unique Base Technologies of Glycoanalysis . . . . . . . . . . . 1379

Hisashi Narimatsu

Contents xxxiii

170 Enigma of Multiple N-Linked Glycoforms of Prostate

Specific Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1387

Richard R. Drake

171 Mammalian Sialidase Assays . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1395

Taeko Miyagi, Kohta Takahashi, Kazuhiro Shiozaki, and

Kazunori Yamaguchi

172 Glycans Against NK Tumor Immunity . . . . . . . . . . . . . . . . . . . . 1403

Shigeru Tsuboi

173 Hyaluronan: Cancer and Cancer Metastasis . . . . . . . . . . . . . . . . 1411

Theerawut Chanmee, Pawared Ontong, and Naoki Itano

174 Sialic Acid and Cancer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1419

Sylvain Julien and Philippe Delannoy

175 Mouse Models of Cancer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1425

Yuzuru Ikehara

176 Mucin and Cancer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1431

Hiroshi Nakada

Part XV iPS Development and Differentiation: Role ofGlycans in iPS and Stem Cell Markers . . . . . . . . . . . . . . . . . . . . . . . 1439

177 Glycomarkers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1441

J. Michael Pierce

178 rBC2LCN: Novel Lectin Probe for Human Pluripotent

Stem Cells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1449

Hiroaki Tateno

179 Novel Antibody for Keratan Sulfate Expressed on

Human iPS/ES Cells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1457

Toshisuke Kawasaki, Nobuko Kawasaki, Hiromi Nakao, and

Hidenao Toyoda

180 Glycan Functions and Signals in Embryonic Stem Cells . . . . . . . 1465

Shoko Nishihara

181 Glycotranscriptomics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1475

Alison Nairn and Kelley Moremen

182 Glycoantigen and Xenotransplantation . . . . . . . . . . . . . . . . . . . . 1483

Akira Maeda, Hiroshi Eguchi, Takuji Kawamura,

Hiroomi Okuyama, and Shuji Miyagawa

183 Glycosaminoglycans in Embryonic and Induced Pluripotent

Stem Cells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1493

Hidenao Toyoda and Akiko-Kinoshita Toyoda

xxxiv Contents

Part XVI Glycotherapeutics: Application of Glycans forTherapeutics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1499

184 Glyco-engineered Therapeutic Antibodies as a

Second-Generation Antibody Therapy . . . . . . . . . . . . . . . . . . . . . 1501

Rinpei Niwa, Kenya Shitara, and Mitsuo Satoh

185 Therapeutic Applications of Sialylated IVIG . . . . . . . . . . . . . . . . 1509

Andrew Pincetic, Jad Maamary, and Jeffrey V. Ravetch

186 Glycomimetic Drugs: Source of Novel Therapeutics . . . . . . . . . . 1517

John L. Magnani

187 Translational Research Using Carbohydrate

Mimetic Peptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1523

Michiko N. Fukuda and Kazuhiro Sugihara

188 Vaccines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1529

Chung-Yi Wu and Chi-Huey Wong

189 Heterologous Glycoprotein Production (Yeast) . . . . . . . . . . . . . . 1537

Yasunori Chiba

190 Heterologous Glycoprotein Production (Plant) . . . . . . . . . . . . . . 1545

Kazuhito Fujiyama

191 Monoclonal Antibodies for Glycans as Tools for Identifying

Endogenous Glycan Ligands for Human

Carbohydrate-Recognition Molecules . . . . . . . . . . . . . . . . . . . . . 1551

Reiji Kannagi and Naoko Kimura

Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1557

Contents xxxv

Contributors

Yoshihiro Akimoto Department of Anatomy, Kyorin University School of

Medicine, Mitaka, Tokyo, Japan

Sayaka Akiyoshi Department of Biological Sciences, Graduate School of Systems

Life Sciences, Kyushu University, Fukuoka, Japan

Hiromune Ando Department of Applied Bio-organic Chemistry, Faculty of

Applied Biological Sciences, Gifu University, Gifu-shi, Gifu, Japan

Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University,

Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto, Japan

Takashi Angata Institute of Biological Chemistry, Academia Sinica, Taipei,

Taiwan

Aristotelis Antonopoulos Department of Life Sciences, Imperial College London,

London, UK

Kazuhiro Aoki Department of Biochemistry and Molecular Biology, Complex

Carbohydrate Research Center, University of Georgia, Athens, GA, USA

Kiyoko F. Aoki-Kinoshita Department of Bioinformatics, Faculty of Engineer-

ing, Soka University, Tokyo, Japan

Hajime Arai Department of Neurosurgery, Juntendo University, Tokyo, Japan

Hiroyuki Arai Department of Geriatrics and Gerontology, Institute of Develop-

ment, Aging and Cancer, Tohoku University, Sendai, Japan

Hisashi Arase Department of Immunochemistry, Research Institute for Microbial

Diseases, Osaka University, Suita, Osaka, Japan

Laboratory of Immunochemistry, WPI Immunology Frontier Research Center,

Osaka University, Suita, Osaka, Japan

CREST, Japan Science and Technology Agency, Kawaguchi, Saitama, Japan

xxxvii

Kimie Asanuma-Date Ochanomizu University, Tokyo, Japan

Brendan J. Beahm Departments of Chemistry, University of California,

Berkeley, CA, USA

Anne K. Bergfeld Department of Cellular and Molecular Medicine, University of

California, San Diego, La Jolla, CA, USA

Kirk Bergstrom Cardiovascular Biology Research Program, Oklahoma Medical

Research Foundation, Oklahoma City, OK, USA

Marshall Bern Palo Alto Research Center, Palo Alto, CA, USA

Carolyn R. Bertozzi Departments of Chemistry, University of California,

Berkeley, CA, USA

Departments of Molecular and Cell Biology, University of California, Berkeley,

CA, USA

Howard Hughes Medical Institute, Chevy Chase, MD, USA

Ada G. Blidner Laboratorio de Inmunopatologıa, Instituto de Biologıa y

Medicina Experimental (IBYME), Consejo Nacional de Investigaciones Cientıficas

y Tecnicas (CONICET), Buenos Aires, Argentina

Raphael Bohm Institute for Glycomics, Griffith University, Gold Coast, QLD,

Australia

Andreas Bohne-Lang Medizinische Fakult€at Mannheim Universit€at Heidelberg,EDV/Bibliothek, Mannheim, Germany

Ivo Gomperts Boneca Biology and Genetics of the Bacterial Cell Wall Unit,

Institut Pasteur, Paris cedex 75, France

Inserm, Group Avenir, Paris, France

Geert-Jan Boons Department of Chemistry and Complex Carbohydrate Research

Center, University of Georgia, Athens, GA, USA

C. Fred Brewer Departments of Molecular Pharmacology, and Microbiology and

Immunology, Albert Einstein College of Medicine, Bronx, NY, USA

Kevin P. Campbell Howard Hughes Medical Institute, Department of Molecular

Physiology and Biophysics, Department of Neurology, Department of Internal

Medicine, University of Iowa Roy J. and Lucille A. Carver College of Medicine,

Iowa City, IA, USA

Matthew P. Campbell Biomolecular Frontiers Research Centre, Macquarie

University, North Ryde, NSW, Sydney, Australia

Theerawut Chanmee Institute of Advanced Technology, Kyoto Sangyo Univer-

sity, Kita-ku, Kyoto, Japan

xxxviii Contributors

Yasunori Chiba Glycomedicine Technology Research Center, National Institute

of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan

Robert A. Childs Glycosciences Laboratory, Department of Medicine, Imperial

College London, London, UK

Zoiesha Chinoy Department of Chemistry and Complex Carbohydrate Research

Center, University of Georgia, Athens, GA, USA

Jin Won Cho Department of Integrated OMICS for Biomedical Science, WCU

Program of Graduate School, Yonsei University, Seoul, South Korea

Henrik Clausen Center for Glycomics, Departments of Cellular and Molecular

Medicine and School of Dentistry, Faculty of Health Sciences, University of

Copenhagen, Copenhagen, Denmark

Brian A. Cobb Department of Pathology, Case Western Reserve University

School of Medicine, Cleveland, OH, USA

David Crich Wayne State University, Detroit, MI, USA

Richard D. Cummings Department of Biochemistry, Emory University School of

Medicine, Atlanta, GA, USA

Nancy M. Dahms Department of Biochemistry, Medical College of Wisconsin,

Milwaukee, WI, USA

Cecilia D’Alessio Laboratory of Glycobiology, Fundacion Instituto Leloir,

Buenos Aires, Argentina

Philippe Delannoy Structural and Functional Glycobiology Unit, University of

Sciences and Technologies of Lille, Villeneuve d’Ascq, France

Anne Dell Department of Life Sciences, Imperial College London, London, UK

Demetria M. Dickinson Department of Chemistry and Chemical Biology, Center

for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute,

Troy, NY, USA

Richard R. Drake Department of Cell and Molecular Pharmacology, Medical

University of South Carolina, Charleston, SC, USA

Kurt Drickamer Department of Life Sciences, Imperial College, London, UK

Danielle H. Dube Department of Chemistry & Biochemistry, Bowdoin College,

Brunswick, ME, USA

Ksenia Egorova N.D. Zelinsky Institute of Organic Chemistry, Russian Academy

of Sciences, Moscow, Russia

Hiroshi Eguchi Division of Organ Transplantation, Department of Surgery,

Osaka University Graduate School of Medicine, Suita, Osaka, Japan

Contributors xxxix

Tamao Endo Tokyo Metropolitan Institute of Gerontology, Tokyo Metropolitan

Geriatric Hospital and Institute of Gerontology, Tokyo, Japan

Junqiang Fang National Glycoengineering Research Center and The State Key

Laboratory of Microbial Technology, Shandong University, Jinan, Shandong,

People’s Republic of China

Ten Feizi Glycosciences Laboratory, Department of Medicine, Imperial College

London, London, UK

Martin Frank Biognos AB, Goteborg, Sweden

Jianxin Fu Cardiovascular Biology Research Program, Oklahoma Medical

Research Foundation, Oklahoma City, OK, USA

Yukari Fujimoto Department of Chemistry, Faculty of Science and Technology,

Keio University, Yokohama, Kanagawa, Japan

Akiko Fujita Department of Biochemistry, University of Texas Southwestern

Medical Center, Dallas, TX, USA

Hideshi Fujiwake Shimadzu Corporation, Kyoto, Japan

Kazuhito Fujiyama International Center for Biotechnology, Osaka University,

Suita, Osaka, Japan

Koichi Fukase Department of Chemistry, Graduate School of Science, Osaka

University, Toyonaka-shi, Osaka, Japan

Michiko N. Fukuda Cancer Center, Sanford-Burnham Medical Research

Institute, La Jolla, CA, USA

Minoru Fukuda Cancer Center, Sanford-Burnham Medical Research Institute,

La Jolla, CA, USA

Tomohiko Fukuda Division of Regulatory Glycobiology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai,

Miyagi, Japan

Katsutoshi Furukawa Department of Geriatrics and Gerontology, Institute of

Development, Aging and Cancer, Tohoku University, Sendai, Japan

Keiko Furukawa Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Department of Biomedical Sciences, College of Life and Health Sciences, Chubu

University, Kasugai, Aichi, Japan

Kiyoshi Furukawa Laboratory of Glycobiology, Department of Bioengineering,

Graduate School of Engineering, Nagaoka University of Technology, Niigata, Japan

Koichi Furukawa Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

xl Contributors

Takashi J. Fuwa Laboratory of Cell Biology, Department of Bioinformatics,

Faculty of Engineering, Soka University, Hachioji, Tokyo, Japan

Congxiao Gao RIKEN-ISIR Osaka University Alliance Lab, The Institute of

Scientific and Industrial Research, Osaka University, Ibaraki, Osaka, Japan

Juan J. Garcia-Vallejo Department of Molecular Cell Biology and Immunology,

VU University Medical Center, Amsterdam, The Netherlands

Elisabeth Gasteiger Swiss-Prot Group, Swiss Institute of Bioinformatics,

Geneva, Switzerland

Ted J. Gauthier AgCenter Biotechnology Laboratory, LSU AgCenter, Baton

Rouge, LA, USA

Satoshi Goto Department of Life Science, Rikkyo University, Toshima-ku,

Tokyo, Japan

Jianguo Gu Division of Regulatory Glycobiology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai,

Miyagi, Japan

Jianxin Gu Department of Biochemistry and Molecular Biology, Basic Medicine

College, Fudan University; Key Laboratory of Glycoconjuates Research, Ministry

of Health, Xuhui District, Shanghai, People’s Republic of China

Huabei Guo Department of Biochemistry and Molecular Biology and Complex

Carbohydrate Research Center, University of Georgia, Athens, GA, USA

Brian Haab Van Andel Research Institute, Grand Rapids, MI, USA

Yoshimi Haga Glycometabolome Team, Systems Glycobiology Research Group,

RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, RIKEN

Global Research Cluster, Wako, Saitama, Japan

Amanda R. Haltom Department of Molecular and Human Genetics, Baylor

College of Medicine, Houston, TX, USA

Program in Genes and Development, University of Texas Health Science Center at

Houston, Houston, TX, USA

Shinya Hanashima Structural Glycobiology Team, Systems Glycobiology

Research Group, RIKEN-Max Planck Joint Research Center, RIKEN Global

Research Cluster, Wako, Saitama, Japan

Department of Chemistry, Graduate School of Science, Osaka University,

Toyonaka, Osaka, Japan

Masaya Hane Bioscience and Biotechnology Center, Nagoya University,

Chikusa, Nagoya, Japan

Contributors xli

Graduate School of Bioagricultural Sciences and School of Agricultural Sciences,

Department of Bioengineering Sciences, Nagoya University, Chikusa, Nagoya,

Japan

Qinglei Hang Division of Regulatory Glycobiology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai,

Miyagi, Japan

Yuji Hara Department of Synthetic Chemistry and Biological Chemistry,

Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan

Tokyo Women’s Medical University Institute for Integrated Medical Sciences,

Shinjuku-ku, Tokyo, Japan

Gerald W. Hart Department of Biological Chemistry, Johns Hopkins University,

School of Medicine, Baltimore, MD, USA

Thomas Haselhorst Institute for Glycomics, Griffith University, Gold Coast,

QLD, Australia

Noboru Hashimoto Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Yasuhiro Hashimoto Department of Biochemistry, Fukushima Medical Univer-

sity School of Medicine, Fukushima, Japan

Stuart M. Haslam Department of Life Sciences, Imperial College London,

London, UK

Jun Hirabayashi Research Center for Stem Cell Engineering, National Institute

of Advanced Industrial Science and Technology, Tsukuba, Ibaraki, Japan

Yoshio Hirabayashi Molecular Membrane Neuroscience, RIKEN Brain Science

Institute, Wako-shi, Saitama, Japan

Noritaka Hirohashi Oki Marine Biological Station, Education and Research

Center for Biological Resources, Shimane University, Oki, Shimane, Japan

Hironobu Hojo Osaka University, Osaka, Japan

Takashi Honda Department of Human Life Science, School of Nursing,

Fukushima Medical University School of Medicine, Fukushima, Japan

Koichi Honke Department of Biochemistry, Kochi University Medical School,

Nankoku, Kochi, Japan

Kyoka Hoshi Department of Biochemistry, Fukushima Medical University

School of Medicine, Fukushima, Japan

Shang-Cheng Hung Genomics Research Center, Academia Sinica, Taipei,

Nangang, Taiwan

Julia H€utter Max Planck Institute of Colloids and Interfaces, Potsdam, Germany

xlii Contributors

Hideyuki Ihara Division of Molecular Cell Biology, Department of Biomolecu-

lar, Sciences, Saga University Faculty of Medicine, Saga, Japan

Yoshito Ihara Department of Biochemistry, Wakayama Medical University

School of Medicine, Wakayama, Japan

Yoshitaka Ikeda Division of Molecular Cell Biology, Department of Biomolec-

ular, Sciences, Saga University Faculty of Medicine, Saga, Japan

Yuzuru Ikehara Diagnostic Pathologist Molecular Medicine, Team of Research

Center for Medical Glycoscience, National Institute for Advanced Industrial

Science and Technology (AIST), Tsukuba, Ibaraki, Japan

Kazuhiro Ikenaka Division of Neurobiology and Bioinformatics, National Insti-

tute for Physiological Sciences, National Institutes of Natural Sciences, Aichi,

Japan

Midori Ikezaki Department of Biochemistry, Wakayama Medical University

School of Medicine, Wakayama, Japan

Juan M. Ilarregui Department of Molecular Cell Biology and Immunology,

VU University Medical Center, Amsterdam, The Netherlands

Akihiro Imamura Department of Applied Bio-organic Chemistry, Faculty of

Applied Biological Sciences, Gifu University, Gifu-shi, Gifu, Japan

Toru Imamura Signaling Molecules Research Group, Biomedical Research Insti-

tute, National Institute of Advanced Industrial Science and Technology (AIST),

Tsukuba, Ibaraki, Japan

Cell Regulation Laboratory, School of Bioscience and Biotechnology, Tokyo

University of Technology, Hachioji, Tokyo, Japan

Anne Imberty Centre de Recherche sur les Macromolecules Vegetales

(CERMAV-CNRS), Grenoble cedex 9, France

Yoko Inai Department of Biochemistry, Wakayama Medical University School of

Medicine, Wakayama, Japan

Jin-ichi Inokuchi Division of Glycopathology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Aoba-ku,

Sendai, Miyagi, Japan

Fumitoshi Irie Human Genetics Program, Sanford-Burnham Medical Research

Institute, La Jolla, CA, USA

Tomoya Isaji Division of Regulatory Glycobiology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai,

Miyagi, Japan

Hideharu Ishida Department of Applied Bio-organic Chemistry, Faculty of

Applied Biological Sciences, Gifu University, Gifu-shi, Gifu, Japan

Contributors xliii

Takeshi Ishimizu Department of Biotechnology, College of Life Sciences,

Ritsumeikan University, Kusatsu, Shiga, Japan

Akira Ishio Department of Biological Sciences, Osaka University, Toyonaka,

Osaka, Japan

Naoki Itano Institute of Advanced Technology, Kyoto Sangyo University,

Kita-ku, Kyoto, Japan

Division of Engineering (Biotechnology), Graduate School of Engineering, Kyoto

Sangyo University, Kita-ku, Kyoto, Japan

Department of Molecular Biosciences, Faculty of Life Sciences, Kyoto Sangyo

University, Kita-ku, Kyoto, Japan

Hiromi Ito Department of Biochemistry, Fukushima Medical University School

of Medicine, Fukushima, Japan

Yuki Ito Cancer Center, Sanford-Burnham Medical Research Institute, Torrey,

CA, USA

Department of Pathology, Ehime University Proteo-Science Center and Graduate

School of Medicine, Toon, Japan

Yukishige Ito Synthetic Cellular Chemistry Laboratory, RIKEN (The Institute of

Physical and Chemical Research), Wako, Saitama, Japan

ERATO, Japan Science and Technology Agency (JST), Ito Glycotrilogy Project,

Wako, Saitama, Japan

Yutaka Itokazu Department of Neuroscience and Regenerative Medicine,

Medical College of Georgia, Georgia Regents University, Augusta, GA, USA

Charlie Norwood VA Medical Center, Augusta, GA, USA

Mark von Itzstein Institute for Glycomics, Griffith University, Gold Coast, QLD,

Australia

Kazuhisa Iwabuchi Laboratory of Biochemistry, Juntendo University School of

Health Care and Nursing, Urayasu, Japan

Institute for Environmental and Gender-specific Medicine, Juntendo University

Graduate School of Medicine, Chiba, Japan

Infection Control Nursing, Juntendo University Graduate School of Health Care

and Nursing, Chiba, Japan

Yoichiro Iwakura Center for Animal Disease Models, Research Institute for

Biomedical Science, Tokyo University of Science, Noda, Chiba, Japan

xliv Contributors

Core Research for Evolutional Science and Technology (CREST), Japan Science

and Technology Agency (JST), Saitama, Japan

Masayuki Izumi Department of Chemistry, Osaka University, Toyonaka, Japan

Hamed Jafar-Nejad Department of Molecular and Human Genetics, Baylor

College of Medicine, Houston, TX, USA

Department of Molecular and Human Genetics, Program in Developmental

Biology, Baylor College of Medicine, Houston, TX, USA

Jianhai Jiang Department of Biochemistry and Molecular Biology, Basic Medi-

cine College, Fudan University; Key Laboratory of Glycoconjuates Research,

Ministry of Health, Xuhui District, Shanghai, People’s Republic of China

Timo Johannssen Max Planck Institute of Colloids and Interfaces, Potsdam,

Germany

Hiren J. Joshi Center for Glycomics, Departments of Cellular and Molecular

Medicine and School of Dentistry, Faculty of Health Sciences, University of

Copenhagen, Copenhagen, Denmark

Sylvain Julien Structural and Functional Glycobiology Unit, University of

Sciences and Technologies of Lille, Villeneuve d’Ascq, France

Kazuya Kabayama Department of Chemistry, Graduate School of Science,

Osaka University, Toyonaka, Osaka, Japan

Kenji Kadomatsu Department of Biochemistry, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Hiroyuki Kaji Glycomedicine Technology Research Center (GTRC), National

Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki,

Japan

Yasuhiro Kajihara Department of Chemistry, Osaka University, Toyonaka, Japan

Kazuaki Kakehi School of Pharmacy, Kinki University, Higashi-osaka, Japan

Yoshihiro Kamada Department of Molecular Biochemistry and Clinical Investi-

gation, Osaka University Graduate School of Medicine, Suita, Japan

Akihiko Kameyama Advanced Glycoscience Research Group, Bioproduction

Research Institute, National Institute of Advanced Industrial Science and Technol-

ogy (AIST), Tsukuba, Ibaraki, Japan

Keisuke Kamimura Department of Brain Development and Neural Regenera-

tion, Tokyo Metropolitan Institute of Medical Science, Setagaya-ku, Tokyo,

Japan

Contributors xlv

Takeru Kanazawa Graduate School of Bioagricultural Sciences, Nagoya Univer-

sity, Nagoya, Japan

Bioscience and Biotechnology Center, Nagoya University, Nagoya, Japan

Reiji Kannagi The Institute of Biomedical Sciences (IBMS), Academia Sinica,

Taipei, Taiwan

Advanced Medical Research Center, Aichi Medical University, Nagakute, Aichi,

Japan

Yoshinobu Kariya Department of Biochemistry, Fukushima Medical University

School of Medicine, Fukushima, Japan

Kohji Kasahara Laboratory of Biomembrane, Tokyo Metropolitan Institute of

Medical Science, Tokyo, Japan

Koichi Kato Institute for Molecular Science and Okazaki Institute for Integrative

Bioscience, Myodaiji, Okazaki, Japan

Graduate School of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku,

Nagoya, Japan

The Glycoscience Institute, Ochanomizu University, Bunkyo-ku, Tokyo, Japan

Ryuichi Kato Structural Biology Research Center, Phptn Factory, Institute of

Materials Structure Science, High Energy Accelerator Research Organization

(KEK), Tsukuba, Ibaraki, Japan

Toshihiko Katoh Research Institute for Bioresources and Biotechnology,

Ishikawa Prefectural University, Nonoichi, Ishikawa, Japan

Hayato Kawakami Department of Anatomy, Kyorin University School of Med-

icine, Mitaka, Tokyo, Japan

Masatomo Kawakubo Department of Molecular Pathology, Shinshu University

Graduate School of Medicine, Matsumoto, Japan

Takuji Kawamura Division of Organ Transplantation, Department of Surgery,

Osaka University Graduate School of Medicine, Suita, Osaka, Japan

Toshisuke Kawasaki Research Center for Glycobiotechnology, Ritsumeikan

University, Kusatsu, Shiga, Japan

Nobuko Kawasaki Research Center for Glycobiotechnology, Ritsumeikan

University, Kusatsu, Shiga, Japan

Hiroto Kawashima Department of Biochemistry, School of Pharmacy and

Pharmaceutical Sciences, Hoshi University, Tokyo, Japan

Carsten Kettner Beilstein-Institut zur Forderung der Chemischen

Wissenschaften, Frankfurt am Main, Germany

Khaled Khatib Glycoinformatics Inc., Great Falls, VA, USA

xlvi Contributors

Kay-Hooi Khoo Academia Sinica, Institute of Biological Chemistry, Taipei, Taiwan

Naoko Kimura Division of Molecular Pathology, Aichi Cancer Center, Nagoya,

Aichi, Japan

Mitsuhiro Kinoshita School of Pharmacy, Kinki University, Higashi-osaka, Japan

Taroh Kinoshita WPI Immunology Frontier Research Center, Osaka University,

Suita, Osaka, Japan

Makoto Kiso Department of Applied Bio-organic Chemistry, Faculty of Applied

Biological Sciences, Gifu University, Gifu-shi, Gifu, Japan

Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University,

Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto, Japan

Hiroshi Kitagawa Department of Biochemistry, Kobe Pharmaceutical University,

Higashinada-ku, Kobe, Japan

Ken Kitajima Bioscience and Biotechnology Center, Nagoya University,

Chikusa, Nagoya, Japan

Department of Bioengineering Sciences, Graduate School of Bioagricultural

Sciences, Nagoya University, Chikusa, Nagoya, Japan

Shinobu Kitazume Disease Glycomics Team, RIKEN-Max Planck Joint

Research Center, Global Research Cluster, RIKEN, Wako, Saitama, Japan

Yasuhiko Kizuka Systems Glycobiology Research Group, RIKEN, Global

Research Cluster, Wako-Shi, Saitama, Japan

Doron Kletter Palo Alto Research Center, Palo Alto, CA, USA

Atsushi Kobayashi Department of Biomolecular Engineering, Graduate School

of Engineering, Tohoku University, Sendai, Japan

Daisuke Kohda Division of Structural Biology, Medical Institute of

Bioregulation, Kyushu University, Fukuoka, Japan

Jennifer J. Kohler Department of Biochemistry, University of Texas Southwest-

ern Medical Center, Dallas, TX, USA

Ayako Kohyama-Koganeya Molecular Membrane Neuroscience, RIKEN Brain

Science Institute, Wako-shi, Saitama, Japan

Takuya Koie Department of Urology, Hirosaki University Graduate School of

Medicine, Hirosaki, Japan

Hisao Kojima Department of Bioinformatics, The College of Life Science,

Ritsumeikan University, Kyoto, Japan

Daniel Kolarich Department of Biomolecular Systems, Max Planck Institute of

Colloids and Interfaces, Potsdam, Germany

Contributors xlvii

Hiroaki Korekane Systems Glycobiology Research Group, RIKEN-Max Planck

Joint Research Center, RIKEN Global Research Cluster, Wako, Saitama, Japan

Norihiro Kotani Department of Biochemistry, Saitama Medical University,

Iruma-gun, Saitama, Japan

Jasminka Kristic Genos Glycoscience, Zagreb, Croatia

Takashi Kudo Department of Anatomy and Embryology, Faculty of Medicine,

University of Tsukuba, Tsukuba, Japan

Laboratory Animal Resource Center (LARC), University of Tsukuba, Tsukuba,

Japan

Amit Kumar Department of Chemistry, Indian Institute of Technology, Patna,

India

Akira Kurosaka Department of Molecular Biosciences, Faculty of Life Sciences,

Kyoto Sangyo University, Kita-ku, Kyoto, Japan

Gordan Lauc Genos Glycoscience, Zagreb, Croatia

Department of Biochemistry and Molecular Biology, Faculty of Pharmacy and

Biochemistry, University of Zagreb, Zagreb, Croatia

Tom V. Lee Department of Molecular and Human Genetics, Baylor College of

Medicine, Houston, TX, USA

Bernd Lepenies Max Planck Institute of Colloids and Interfaces, Potsdam,

Germany

Xuechen Li Department of Chemistry, The University of Hong Kong, Hong

Kong, People’s Republic of China

Robert J. Linhardt Department of Chemistry and Chemical Biology, Center for

Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute,

Troy, NY, USA

Frederique Lisacek Proteome Informatics Group, Swiss-Prot Group, Swiss

Institute of Bioinformatics, Geneva, Switzerland

Section of Biology, Faculty of Sciences, University of Geneva, Switzerland

Jian Liu Division of Chemical Biology and Medicinal Chemistry, Eshelman

School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA

Yan Liu Glycosciences Laboratory, Department of Medicine, Imperial College

London, London, UK

Yunpeng Liu National Glycoengineering Research Center and The State Key

Laboratory of Microbial Technology, Shandong University, Jinan, Shandong,

People’s Republic of China

xlviii Contributors

Alexander Loss Gebr€uder Gerstenberg GmbH & Co. KG, EDV, Hildesheim,

Germany

Thomas L€utteke Institute of Veterinary Physiology and Biochemistry, Justus-

Liebig-University Giessen, Giessen, Germany

Jad Maamary Laboratory of Molecular Genetics and Immunology, The Rocke-

feller University, New York, NY, USA

Akira Maeda Division of Organ Transplantation, Department of Surgery, Osaka

University Graduate School of Medicine, Suita, Osaka, Japan

Nobuaki Maeda Department of Brain Development and Neural Regeneration,

Tokyo Metropolitan Institute of Medical Science, Setagaya-ku, Tokyo, Japan

Yusuke Maeda Department of Immunoregulation, Research Institute for Micro-

bial Diseases, Osaka University, Suita, Osaka, Japan

John L. Magnani Department of Biochemistry and Drug Discovery,

GlycoMimetics, Gaithersburg, MD, USA

Hisayoshi Makyio Structural Biology Research Center, Phptn Factory, Institute of

Materials Structure Science, High Energy Accelerator Research Organization

(KEK), Tsukuba, Ibaraki, Japan

Shino Manabe Synthetic Cellular Chemistry Laboratory, RIKEN, Wako,

Saitama, Japan

Julien Mariethoz Proteome Informatics Group, Swiss-Prot Group, Swiss Institute

of Bioinformatics, Geneva, Switzerland

Ayako Matsuda Department of Biological Sciences, Graduate School of Systems

Life Sciences, Kyushu University, Fukuoka, Japan

In-Sook L. Matsui Department of Biochemistry, Wakayama Medical University

School of Medicine, Wakayama, Japan

Kenjiroo Matsumoto Department of Biological Sciences, Osaka University,

Toyonaka, Osaka, Japan

Shunsuke Matsumoto Faculty of Life Sciences, Kyoto Sangyo University,

Kyoto, Japan

Yuka Matsumoto Department of Neurosurgery, Fukushima Medical University

School of Medicine, Fukushima, Japan

Kenji Matsuno Department of Biological Sciences, Osaka University, Toyonaka,

Osaka, Japan

Yu-ki Matsuno Advanced Glycoscience Research Group, Bioproduction

Research Institute, National Institute of Advanced Industrial Science and Technol-

ogy (AIST), Tsukuba, Ibaraki, Japan

Contributors xlix

TadahisaMikami Department of Biochemistry, Kobe Pharmaceutical University,

Higashinada-ku, Kobe, Japan

Yuri Miura Research Team for Mechanism of Aging, Tokyo Metropolitan

Institute of Gerontology, Itabashi-ku, Tokyo, Japan

Shuji Miyagawa Division of Organ Transplantation, Department of Surgery,

Osaka University Graduate School of Medicine, Suita, Osaka, Japan

Taeko Miyagi Cancer Glycosylation Research, Tohoku Pharmaceutical Univer-

sity, Sendai, Japan

Masakazu Miyajima Department of Neurosurgery, Juntendo University, Tokyo,

Japan

Kensuke Miyake The Institute of Medical Science, The University of Tokyo,

Tokyo, Japan

Yasuhide Miyamoto Department of Immunology, Osaka Medical Center for

Cancer and Cardiovascular Diseases, Osaka, Japan

Shinji Miyata Graduate School of Bioagricultural Sciences, Nagoya University,

Nagoya, Japan

Bioscience and Biotechnology Center, Nagoya University, Nagoya, Japan

Institute for Advanced Research, Nagoya University, Nagoya, Japan

Eiji Miyoshi Department of Molecular Biochemistry and Clinical Investigation,

Osaka University Graduate School of Medicine, Suita, Japan

Kelley Moremen Complex Carbohydrate Research Center, The University of

Georgia, Athens, GA, USA

P. A. S. Mourao University Hospital Clementino Fraga Filho, Federal University

of Rio de Janeiro, Rio de Janeiro, Brazil

Elaine Mullen The MITRE Corporation, McLean, VA, USA

Yoshiko Murakami Department of Immunoregulation, Research Institute for

Microbial Diseases, Osaka University, Suita, Osaka, Japan

Masakazu Nagafuku Division of Glycopathology, Institute of Molecular

Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Aoba-ku,

Sendai, Miyagi, Japan

Alison Nairn Complex Carbohydrate Research Center, The University of Geor-

gia, Athens, GA, USA

Hiroshi Nakada Department of Molecular Biosciences, Faculty of Life Sciences,

Kyoto Sangyo University, Kyoto, Japan

Naoki Nakagawa Department of Biological Chemistry, Human Health Sciences,

Graduate School of Medicine, Kyoto University, Sakyo-ku, Kyoto, Japan

l Contributors

Kazuki Nakajima Molecular Membrane Neuroscience, RIKEN Brain Science

Institute, Wako-shi, Saitama, Japan

Naosuke Nakamura Department of Molecular Biosciences, Faculty of Life Sci-

ences, Kyoto Sangyo University, Kita-ku, Kyoto, Japan

Sachiko Nakamura-Tsuruta Venture Business Laboratory, Kagoshima Univer-

sity, Kagoshima, Japan

Hiromi Nakao Research Center for Glycobiotechnology, Ritsumeikan University,

Kusatsu, Shiga, Japan

Hiroshi Nakato University of Minnesota, Minneapolis, MN, USA

Hitoshi Nakayama Laboratory of Biochemistry, Juntendo University School of

Health Care and Nursing, Urayasu, Japan

Institute for Environmental and Gender-specific Medicine, Juntendo University

Graduate School of Medicine, Chiba, Japan

Jun Nakayama Department of Molecular Pathology, Shinshu University Gradu-

ate School of Medicine, Matsumoto, Japan

Yoshiaki Nakayama Department of Molecular Biosciences, Faculty of Life Sci-

ences, Kyoto Sangyo University, Kita-ku, Kyoto, Japan

Hisashi Narimatsu Glycomedicine Technology Research Center (GTRC),

National Institute of Advanced Industrial Science and Technology (AIST),

Tsukuba, Japan

Hisashi Narimatsu Glycomedicine Technology Research Center, Advanced

Industrial Science and Technology (AIST), Tsukuba, Japan

Hisashi Narimatsu Open Space Lab, Glycomedicine Technology Research Cen-

ter (GTRC), National Institute of Advanced Industrial Science and Technology

(AIST), Tsukuba, Ibaraki, Japan

Shoko Nishihara Laboratory of Cell Biology, Department of Bioinformatics,

Faculty of Engineering, Soka University, Hachioji, Tokyo, Japan

Atsushi Nishikawa Department of Applied Biological Science, Tokyo University

of Agriculture and Technology, Fuchu-shi, Tokyo, Japan

Rinpei Niwa Kyowa Hakko Kirin Co., Ltd, Chiyoda-ku, Tokyo, Japan

Masato Noguchi Department of Biomolecular Engineering, Graduate School of

Engineering, Tohoku University, Sendai, Japan

Kazuko H. Nomura Department of Biological Sciences, Graduate School of

Systems Life Sciences, Kyushu University, Fukuoka, Japan

Kazuya Nomura Department of Biological Sciences, Graduate School of Systems

Life Sciences, Kyushu University, Fukuoka, Japan

Contributors li

Motohiro Nonaka Cancer Center, Sanford-Burnham Medical Research Institute,

La Jolla, CA, USA

James Nyirenda Department of Chemistry, University of Zambia, Lusaka,

Zambia

Haruko Ogawa Ochanomizu University, Tokyo, Japan

Mitsutaka Ogawa Department of Bioscience, Nagahama Institute of Bio-Science

and Technology, Nagahama, Shiga, Japan

Keiji Oguma Asahi Medical College Group, Kita-ku, Okayama, Japan

Yuki Ohkawa Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Yuhsuke Ohmi Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Katsuyuki Ohmori Department of Clinical Pathology, Kyoto University School

of Medicine, Kyoto, Japan

Shiro Ohshima Clinical Research, Osaka Minami Medical Center,

Kawachinagano, Osaka, Japan

Katsuki Ohtani Department of Microbiology and Immunochemistry, Asahikawa

Medical University, Asahikawa, Japan

Kazuaki Ohtsubo Kumamoto University, Kumamoto, Japan

Chikara Ohyama Department of Urology, Hirosaki University Graduate School

of Medicine, Hirosaki, Japan

Shogo Oka Department of Biological Chemistry, Human Health Sciences,

Graduate School of Medicine, Kyoto University, Sakyo-ku, Kyoto, Japan

Takahiro Okada Division of Molecular Cell Biology, Department of Biomolec-

ular, Sciences, Saga University Faculty of Medicine, Saga, Japan

Tetsuya Okajima Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Ryo Okamoto Department of Chemistry, Osaka University, Toyonaka, Japan

Shujiro Okuda Niigata University Graduate School of Medical and Dental

Sciences, Niigata, Japan

Toshiomi Okuno Department of Microbiology, Hyogo College of Medicine,

Nishinomiya, Hyogo, Japan

Hiroomi Okuyama Division of Organ Transplantation, Department of Surgery,

Osaka University Graduate School of Medicine, Suita, Osaka, Japan

lii Contributors

Linda J. Olson Department of Biochemistry, Medical College of Wisconsin,

Milwaukee, WI, USA

Pawared Ontong Division of Engineering (Biotechnology), Graduate School of

Engineering, Kyoto Sangyo University, Kita-ku, Kyoto, Japan

Michel Ouellet Research Centre for Infectious Diseases, Centre de Recherche du

CHU de Quebec, Pavillon CHUL, Quebec, Quebec, Canada

Faculty of Medicine, Laval University, Quebec, Quebec, Canada

Nicolle H. Packer Biomolecular Frontiers Research Centre, Macquarie

University, North Ryde, NSW, Sydney, Australia

Poh-Choo Pang Department of Life Sciences, Imperial College London, London,

UK

Sujin Park Department of Integrated OMICS for Biomedical Science, WCU

Program of Graduate School, Yonsei University, Seoul, South Korea

Jong Yi Park Gyeongbuk Institute for Bioindustry, Andong-si, Gyeongbuk, South

Korea

Armando J. Parodi Laboratory of Glycobiology, Fundacion Instituto Leloir,

Buenos Aires, Argentina

Katharina Paschinger Department f€ur Chemie, Universit€at f€ur Bodenkultur,

University of Natural Resources and Life Sciences, Wien, Austria

Serge Perez Centre de Recherche sur les Macromolecules Vegetales (CERMAV-

CNRS), Grenoble cedex 9, France

Robyn Peterson Biomolecular Frontiers Research Centre, Macquarie University,

North Ryde, NSW, Sydney, Australia

J. Michael Pierce Department of Biochemistry and Molecular Biology and Com-

plex Carbohydrate Research Center, University of Georgia, Athens, GA, USA

J. Michael Pierce Department of Biochemistry and Molecular Biology, Complex

Carbohydrate Research Center and UGA Cancer Center, University of Georgia,

Athens, GA, USA

Andrew Pincetic Laboratory of Molecular Genetics and Immunology, The

Rockefeller University, New York, NY, USA

Salome S. Pinho Institute of Molecular Pathology and Immunology of the

University of Porto (IPATIMUP), Porto, Portugal

Institute of Biomedical Sciences of Abel Salazar (ICBAS), University of Porto,

Porto, Portugal

V. H. Pomin Institute of Medical Biochemistry Leopoldo de Meis, Federal

University of Rio de Janeiro, Rio de Janeiro, Brazil

Contributors liii

Gabriel A. Rabinovich Laboratorio de Inmunopatologıa, Instituto de Biologıa y

Medicina Experimental (IBYME), Consejo Nacional de Investigaciones Cientıficas

y Tecnicas (CONICET), Buenos Aires, Argentina

Rene Ranzinger Complex Carbohydrate Research Center, University of Georgia,

Athens, GA, USA

Jeffrey V. Ravetch The Rockefeller University, New York, NY, USA

Celso A. Reis Institute of Molecular Pathology and Immunology of the University

of Porto (IPATIMUP), Porto, Portugal

Institute of Biomedical Sciences of Abel Salazar (ICBAS), University of Porto,

Porto, Portugal

Medical Faculty, University of Porto, Porto, Portugal

Alain Rivet Centre de Recherche sur les Macromolecules Vegetales (CERMAV-

CNRS), Grenoble cedex 9, France

Miguel A. Rojas-Macias Institute of Veterinary Physiology and Biochemistry,

Justus-Liebig-University Giessen, Giessen, Germany

Thomas Ruppert Center for Molecular Biology, University of Heidelberg,

Heidelberg, Germany

Sean O. Ryan Department of Pathology, Case Western Reserve University School

of Medicine, Cleveland, OH, USA

Shinobu Saijo Division of Molecular Immunology, Medical Mycology Research

Center, Chiba University, Chiba, Japan

Precursory Research for Embryonic Science and Technology (PRESTO), JST,

Saitama, Japan

Kiyoshi Saito Department of Neurosurgery, Fukushima Medical University

School of Medicine, Fukushima, Japan

Toshie Saito Department of Biochemistry, Fukushima Medical University School

of Medicine, Fukushima, Japan

Keiichiro Sakuma Division of Molecular Pathology, Aichi Cancer Center,

Nagoya, Aichi, Japan

Annie N. Samraj Department of Cellular and Molecular Medicine, University of

California, San Diego, La Jolla, CA, USA

Kunihiro Sano Institute of Glycoscience, Tokai University, Kanagawa, Japan

liv Contributors

Chihiro Sato Bioscience and Biotechnology Center, Nagoya University, Chikusa,

Nagoya, Japan

Graduate School of Bioagricultural Sciences and School of Agricultural Sciences,

Department of Bioengineering Sciences, Nagoya University, Chikusa, Nagoya,

Japan

Sachiko Sato Research Centre for Infectious Diseases, Centre de Recherche du

CHU de Quebec, Pavillon CHUL, Quebec, Quebec, Canada

Faculty of Medicine, Laval University, Quebec, Quebec, Canada

Takeshi Sato Laboratory of Glycobiology, Department of Bioengineering, Grad-

uate School of Engineering, Nagaoka University of Technology, Niigata, Japan

Mitsuo Satoh Kyowa Hakko Kirin Co., Ltd, Chiyoda-ku, Tokyo, Japan

Katrine T.-B. G. Schjoldager Center for Glycomics, Departments of Cellular and

Molecular Medicine and School of Dentistry, Faculty of Health Sciences, Univer-

sity of Copenhagen, Copenhagen, Denmark

Richard R. Schmidt Universit€at Konstanz, Konstanz, Germany

Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah,

Saudi Arabia

Ronald L. Schnaar Department of Pharmacology and Neuroscience, Johns Hop-

kins University School of Medicine, Baltimore, MD, USA

Akira Seko ERATO Glycotrilogy Project, Japan Science and Technology

Agency, Wako, Saitama, Japan

Toshihide Shikanai Glycomedicine Technology Research Center (GTRC),

National Institute of Advanced Industrial Science and Technology (AIST),

Tsukuba, Japan

Kazuhiro Shiozaki Marine Biochemistry, Kagoshima University, Kagoshima,

Japan

Haruko Shirato Department of Virology II, National Institute of Infectious Dis-

eases, Tokyo, Japan

Kenya Shitara Kyowa Hakko Kirin Co., Ltd, Chiyoda-ku, Tokyo, Japan

Shin-ichiro Shoda Department of Biomolecular Engineering, Graduate School of

Engineering, Tohoku University, Sendai, Japan

Michael Sobel Division of Vascular Surgery, VA Puget Sound Health Care

System and the University of Washington, School of Medicine, Seattle, WA, USA

Contributors lv

Pamela Stanley Department of Cell Biology, Albert Einstein College of Medi-

cine, New York, NY, USA

Catharina Steentoft Center for Glycomics, Departments of Cellular and Molec-

ular Medicine and School of Dentistry, Faculty of Health Sciences, University of

Copenhagen, Copenhagen, Denmark

Sabine Strahl Centre for Organismal Studies, University of Heidelberg, Heidel-

berg, Germany

Yasuo Suda Department of Chemistry Biotechnology and Chemical Engineering,

Graduate School of Science and Engineering, Kagoshima University, Kagoshima,

Japan

SUDx-Biotec Corp, Shiroyama, Kagoshima, Japan

Venture Business Laboratory, Kagoshima University, Kagoshima, Japan

Tadahiro Suenaga Department of Immunochemistry, Research Institute for

Microbial Diseases, Osaka University, Suita, Osaka, Japan

Laboratory of Immunochemistry, WPI Immunology Frontier Research Center,

Osaka University, Suita, Osaka, Japan

Kazuhiro Sugihara Department of Obstetrics and Gynecology, Hamamatsu Uni-

versity School of Medicine, Hamamatsu City, Shizuoka, Japan

Akemi Suzuki Institute of Glycoscience, Tokai University, Kanagawa, Japan

Eriko Suzuki Graduate School of Bioagricultural Sciences, Nagoya University,

Nagoya, Japan

Bioscience and Biotechnology Center, Nagoya University, Nagoya, Japan

Kenichi G. N. Suzuki Institute for Integrated Cell-Material Sciences (WPI-

iCeMS), Kyoto University, Kyoto, Japan

Institute for Stem Cell Biology and Regenerative Medicine, National Centre for

Biological Sciences, Bangalore, India

Minoru Suzuki School of Integrative and Global Majors, Ph.D. Program in

Human Biology, University of Tsukuba, Ibaraki, Japan

Tadashi Suzuki Glycometabolome Team, Systems Glycobiology Research

Group, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology,

RIKEN Global Research Cluster, Wako, Saitama, Japan

Takashi Suzuki Department of Biochemistry, School of Pharmaceutical Sciences,

University of Shizuoka, Shizuoka-shi, Shizuoka, Japan

Yasuhiko Suzuki Division of Bioresources, Hokkaido University Research

Center for Zoonosis Control, Sapporo, Japan

lvi Contributors

Yusuke Suzuki Department of Materials and Applied Chemistry, College of

Science and Technology, Nihon University, Tokyo, Japan

Tomohiko Taguchi Pathological Cell Biology, Graduate School of Pharmaceuti-

cal Sciences, University of Tokyo, Tokyo, Japan

Orie Tajima Department of Biochemistry II, Nagoya University Graduate School

of Medicine, Showa-ku, Nagoya, Japan

Department of Biomedical Sciences, College of Life and Health Sciences, Chubu

University, Kasugai, Aichi, Japan

Satoru Takahashi Department of Anatomy and Embryology, Faculty of Medi-

cine, University of Tsukuba, Tsukuba, Japan

International Institute for Integrative Sleep Medicine (WPI-IIIS), University of

Tsukuba, Tsukuba, Japan

Life Science Center, Tsukuba Advanced Research Alliance (TARA), University of

Tsukuba, Tsukuba, Japan

Laboratory Animal Resource Center (LARC), University of Tsukuba, Tsukuba,

Japan

Kohta Takahashi Cancer Glycosylation Research, Tohoku Pharmaceutical Uni-

versity, Sendai, Japan

Motoko Takahashi Department of Biochemistry, Sapporo Medical University

School of Medicine, Sapporo, Japan

Tadanobu Takahashi Department of Biochemistry, School of Pharmaceutical

Sciences, University of Shizuoka, Shizuoka-shi, Shizuoka, Japan

Rina Takamiya Sapporo Medical University, Sapporo, Japan

Yoichi Takeda ERATO Glycotrilogy Project, Japan Science and Technology

Agency, Wako, Saitama, Japan

Yuichi Takeda Department of Biochemistry, Osaka University Graduate School

of Medicine, Suita, Osaka, Japan

Hiromu Takematsu Department of Biological Chemistry, Human Health Sci-

ences, Graduate School of Medicine, Kyoto University, Kyoto, Japan

Hiroshi Tanaka Department of Applied Chemistry, Graduate School of Science

and Engineering, Tokyo Institute of Technology, Meguro, Tokyo, Japan

Katsunori Tanaka RIKEN, Saitama, Japan

Naoyuki Taniguchi Systems Glycobiology Research Group, RIKEN-Max Planck

Joint Research Center for Systems Chemical Biology, Global Research Cluster,

RIKEN, Saitama, Japan

Osaka University, Osaka, Japan

Contributors lvii

Natsuko Tanimura The Institute of Medical Science, The University of Tokyo,

Tokyo, Japan

Hiroaki Tateno Research Center for Stem Cell Engineering, National Institute of

Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan

Carol M. Taylor Department of Chemistry, Louisiana State University, Baton

Rouge, LA, USA

Maureen E. Taylor Department of Life Sciences, Imperial College, London, UK

Kelly G. Ten Hagen Developmental Glycobiology Section, NIDCR/NIH,

National Institutes of Health, Bethesda, MD, USA

Michael Tiemeyer Department of Biochemistry and Molecular Biology, Com-

plex Carbohydrate Research Center, University of Georgia, Athens, GA, USA

Yuki Tobisawa Department of Urology, Hirosaki University Graduate School of

Medicine, Hirosaki, Japan

Akira Togayachi Glycomedicine Technology Research Center (GTRC), National

Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki,

Japan

Takashi Tonozuka Department of Applied Biological Science, Tokyo University

of Agriculture and Technology, Fuchu-shi, Tokyo, Japan

Philip Toukach N.D. Zelinsky Institute of Organic Chemistry, Russian Academy

of Sciences, Moscow, Russia

Akiko-Kinoshita Toyoda College of Pharmaceutical Sciences, Ritsumeikan

University, Kusatsu, Shiga, Japan

Hidenao Toyoda College of Pharmaceutical Sciences, Ritsumeikan University,

Kusatsu, Shiga, Japan

Van N. Tra Department of Chemistry & Biochemistry, Bowdoin College, Bruns-

wick, ME, USA

Michel J. Tremblay Research Centre for Infectious Diseases, Centre de

Recherche du CHU de Quebec, Pavillon CHUL, Quebec, Quebec, Canada

Faculty of Medicine, Laval University, Quebec, Quebec, Canada

Tsung-I Tsai Genomics Research Center, Academia Sinica, Taipei, Taiwan

Takeshi Tsubata Department of Immunology, Medical Research Institute, Tokyo

Medical and Dental University, Tokyo, Japan

Shigeru Tsuboi Department of Cancer Immunology and Cell Biology, Oyokyo

Kidney Research Institute, Hirosaki, Aomori, Japan

lviii Contributors

Yoshikatsu Umemura Shimadzu Corporation, Kyoto, Japan

Sergey Y. Vakhrushev Center for Glycomics, Departments of Cellular and

Molecular Medicine and School of Dentistry, Faculty of Health Sciences, Univer-

sity of Copenhagen, Copenhagen, Denmark

Yvette van Kooyk Department of Molecular Cell Biology and Immunology, VU

University Medical Center, Amsterdam, The Netherlands

Ajit Varki Department of Cellular and Molecular Medicine, University of

California, San Diego, La Jolla, CA, USA

Frederic Veyrier Biology and Genetics of the Bacterial Cell Wall Unit, Institut

Pasteur, Paris cedex 75, France

Inserm, Group Avenir, Paris, France

Invasive Bacterial Infections Unit, Institut Pasteur, Paris cedex 75, France

Microbiology, Molecular Biology and Evolutionary Biology, Institut Pasteur in

Paris, Paris, France

Ana Cristina E. S. Vilela-Silva Institute of Biomedical Sciences, Federal

University of Rio de Janeiro, Rio de Janeiro, Brazil

Yoshinao Wada Department of Molecular Medicine, Osaka Medical Center and

Research Institute for Maternal and Child Health, Osaka, Japan

Nobutaka Wakamiya Department of Microbiology and Immunochemistry,

Asahikawa Medical University, Asahikawa, Japan

Masahiro Wakao Department of Chemistry Biotechnology and Chemical Engi-

neering, Graduate School of Science and Engineering, Kagoshima University,

Kagoshima, Japan

Hans H. Wandall Center for Glycomics, Departments of Cellular and Molecular

Medicine and School of Dentistry, Faculty of Health Sciences, University of

Copenhagen, Copenhagen, Denmark

Lai-Xi Wang Institute of Human Virology and Department of Biochemistry &

Molecular Biology, University of Maryland School of Medicine, Baltimore, MD,

USA

Peng George Wang Center for Diagnostics & Therapeutics and Department of

Chemistry, Georgia State University, Atlanta, GA, USA

National Glycoengineering Research Center and The State Key Laboratory of

Microbial Technology, Shandong University, Jinan, Shandong, People’s Republic

of China

Contributors lix

Xiangchun Wang Vaccine Production Program Laboratory, Vaccine Research

Center, NIAID, NIH, Bethesda, MD, USA

Hideto Watanabe Institute for Molecular Science of Medicine, Aichi Medical

University, Nagakute, Aichi, Japan

Hanke van der Wel Department of Biochemistry and Molecular Biology, Okla-

homa Center for Medical Glycobiology, Health Sciences Center, University of

Oklahoma, Oklahoma City, OK, USA

Catherine Werts Biology and Genetics of the Bacterial Cell Wall Unit, Institut

Pasteur, Paris cedex 75, France

Inserm, Group Avenir, Paris, France

Christopher M.West Department of Biochemistry and Molecular Biology, Okla-

homa Center for Medical Glycobiology, Health Sciences Center, University of

Oklahoma, Oklahoma City, OK, USA

Richard Wheeler Biology and Genetics of the Bacterial Cell Wall Unit, Institut

Pasteur, Paris cedex 75, France

Inserm, Group Avenir, Paris, France

Iain B. H. Wilson Department f€ur Chemie, Universit€at f€ur Bodenkultur, Univer-sity of Natural Resources and Life Sciences, Wien, Austria

Patrick R. Winterhalter Centre for Organismal Studies, University of Heidel-

berg, Heidelberg, Germany

Center for Molecular Biology, University of Heidelberg, Heidelberg, Germany

Chi-Huey Wong Academia Sinica, Nankang, Taipei, Taiwan

The Scripps Research Institute, La Jolla, CA, USA

Chung-Yi Wu Genomics Research Center, Academia Sinica, Taipei, Taiwan

Zhigang Wu Center for Diagnostics & Therapeutics and Department of Chemis-

try, Georgia State University, Atlanta, GA, USA

Lijun Xia Cardiovascular Biology Research Program, Oklahoma Medical

Research Foundation, Oklahoma City, OK, USA

Department of Biochemistry and Molecular Biology, University of Oklahoma

Health Sciences Center, Oklahoma City, OK, USA

Ci Xu Department of Chemistry, The University of Hong Kong, Hong Kong,

People’s Republic of China

Yuechi Xu Department of Biochemistry and Molecular Biology, Oklahoma

Center for Medical Glycobiology, Health Sciences Center, University of

Oklahoma, Oklahoma City, OK, USA

lx Contributors

Rikio Yabe Center for Animal Disease Models, Research Institute for Biomedical

Science, Tokyo University of Science, Noda, Chiba, Japan

Division of Molecular Immunology, Medical Mycology Research Center, Chiba

University, Chiba, Japan

Kazunori Yamaguchi Miyagi Cancer Center Research Institute, Natori, Japan

Takumi Yamaguchi Institute for Molecular Science and Okazaki Institute for

Integrative Bioscience, Myodaiji, Okazaki, Japan

Graduate School of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku,

Nagoya, Japan

Yoshiki Yamaguchi Structural Glycobiology Team, Systems Glycobiology

Research Group, RIKEN-Max Planck Joint Research Center, RIKEN Global

Research Cluster, Wako, Saitama, Japan

Yu Yamaguchi Human Genetics Program, Sanford-Burnham Medical Research

Institute, La Jolla, CA, USA

Kenji Yamamoto Research Institute for Bioresources and Biotechnology,

Ishikawa Prefectural University, Nonoichi, Ishikawa, Japan

Kazuo Yamamoto Department of Integrated Biosciences, Graduate School of

Frontier Sciences, The University of Tokyo, Kashiwa, Chiba, Japan

Miki Yamamoto-Hino Department of Life Science, Rikkyo University, Toshima-

ku, Tokyo, Japan

Yoshio Yamauchi Department of Biochemistry II, Nagoya University Graduate

School of Medicine, Showa-ku, Nagoya, Japan

Tohru Yoneyama Department of Urology, Hirosaki University Graduate School

of Medicine, Hirosaki, Japan

William S. York Complex Carbohydrate Research Center, University of Georgia,

Athens, GA, USA

Robert K. Yu Department of Neuroscience and Regenerative Medicine, Medical

College of Georgia, Georgia Regents University, Augusta, GA, USA

Charlie Norwood VA Medical Center, Augusta, GA, USA

Zaikuan Yu Center for Diagnostics & Therapeutics and Department of Chemis-

try, Georgia State University, Atlanta, GA, USA

Xu Zhang Department of Chemistry Biotechnology and Chemical Engineering,

Graduate School of Science and Engineering, Kagoshima University, Kagoshima,

Japan

SUDx-Biotec Corp, Shiroyama, Kagoshima, Japan

Contributors lxi

Guohui Zhao Center for Diagnostics & Therapeutics and Department of Chem-

istry, Georgia State University, Atlanta, GA, USA

Lei Zhou Department of Biochemistry and Molecular Biology, Basic Medicine

College, Fudan University; Key Laboratory of Glycoconjuates Research, Ministry

of Health, Xuhui District, Shanghai, People’s Republic of China

Hailiang Zhu Center for Diagnostics & Therapeutics and Department of Chem-

istry, Georgia State University, Atlanta, GA, USA

Stephanie Zimmermann Max Planck Institute of Colloids and Interfaces,

Potsdam, Germany

Vlatka Zoldos Department of Molecular Biology, Faculty of Science, University

of Zagreb, Zagreb, Croatia

Medel Manuel L. Zulueta Genomics Research Center, Academia Sinica, Taipei,

Nangang, Taiwan

lxii Contributors