Jan 2011 NUCLEUS AA2B - Welcome to NESACS - … The Nucleus February 2012 Monday, February 21, I chose to return on a very long Saturday in the reverse direction. I was further advised

http://www.nesacs.org

February 2012 Vol. XC, No. 6

90th Anniversary Issue of The NUCLEUS

NORTHEASTERN SECTION • AMERICAN CHEMIC

ALSO

CIET

Y

FOUNDED 1898

NESACS

MonthlyMeetingCraig F. Ferris, NortheasternUniversity, to speak at the BrooklineHoliday Inn

Report fromBangkokBy Morton Z. Hoffman

SummerScholar ReportNovel Approach to SymmetricalAmino Acid-Derived PeptideIsosteresBy Matthew P. Mower and Craig K.Zercher, University of NewHampshire

2012 RichardsMedal Awardedto Tobin Jay Marks

2 The Nucleus February 2012

In November 2010, I received an e-mail from Nancy Jackson, manager ofthe U.S. Department of State ChemicalSecurity Engagement Program (CSP)at Sandia National Laboratories andthen ACS President-elect, asking if I,or someone else who has connectionswith IUPAC, would be interested inparticipating in a one-week CSSOtraining course for academic/labora-tory chemists from the Mekong Deltaregion (Cambodia, Laos, Vietnam) inBangkok, Thailand, some time early in

2011. I replied, expressing my interestas the U.S. National Representative tothe IUPAC Committee on ChemistryEducation (CCE) to help this CSPactivity in any way, and my willing-ness to participate. [Full disclosure: Ihad never been to Bangkok.] Somedays later, I received a message fromDr. Pauline Ho, a member of the Inter-national Chemical Threat ReductionDepartment at Sandia who organizesthe training courses, describing theevolving plans for the program inBangkok during the upcoming Febru-ary-May period. Dr. Ho and I alsoarranged to meet in Honolulu inDecember at PacifiChem, which weboth would be attending.

It was not until early January that Ilearned that the CSSO training pro-gram would be held Monday-Friday,February 14-18; I was invited to partic-ipate as an IUPAC representative forthis International Year of Chemistryevent, make introductory remarks

about IYC, serve as the resident educa-tional consultant, and conduct smallgroup discussions. I was advised byDr. Ho to contact a member of hertravel staff to make the appropriateflight arrangements, which had toabide by federal government rules:travel on U.S.-carriers into and out ofthe U.S.; business class for long flights(more than 14 hours) or a stop-over,but not both; arrival two days beforethe start of the program to reduce jetlag; personal days could be added tothe trip as desired.

A business class ticket on UnitedAirlines was purchased for me by San-dia; I would leave Boston on the morn-ing of Thursday, February 10, connectin Washington (Dulles) for a nonstopflight to Tokyo with arrival on Fridayafternoon (crossing the InternationalDate Line), and arrive in Bangkok atabout midnight. Because I already hadplans in Boston on my calendar for

Report from BangkokChemical Safety and Security Officer (CSSO) Training WorkshopPhotos and article by Morton Z. Hoffman, Boston University [[email protected]]

Continued on page 4

The Nucleus February 2012 3

The Nucleus is published monthly, except June and August, by the Northeastern Section of the AmericanChemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Textmust be received by the editor six weeks before the date of issue.Editor: Michael P. Filosa, Ph.D., ZINK Imaging, Inc., 16 Crosby Drive, Building 4G,

Bedford, MA 01730 Email: Michael.filosa(at)zink.com; Tel: 508-843-9070Associate Editors: Myron S. Simon, 20 Somerset Rd., W. Newton, MA 02465, Tel: 617-332-5273,

Sheila E Rodman, Konarka Technologies, Inc., 116 John St. Suite 12, Lowell,MA 01852 Email: srodman(at)konarka.com tel 978-569-1414, Mindy Levine, 516-697-9688, mindy.levine(at)gmail.com

Board of Publications: Mary Mahaney (Chair), Mindy Levine, Vivian K. WalworthBusiness Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050,

Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book Reviews Calendar Coordinator: Sheila Rodman, email: srodman(at)konarka.comPhotographers: Morton Z. Hoffman and James PhillipsProofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy Levine Webmaster: Roy HagenCopyright 2012, Northeastern Section of the American Chemical Society, Inc.

The Northeastern Section of the AmericanChemical Society, Inc.Office: Anna Singer, 12 Corcoran Road,Burlington, MA 01803(Voice or FAX) 781-272-1966.e-mail: secretary(at)nesacs.orgNESACS Homepage:http://www.NESACS.orgOfficers 2012ChairRuth TannerOlney Hall 415BLowell, MA 01854University of Mass LowellRuth_Tanner(at)uml.edu978-934-3662Chair-ElectLiming ShaoSunovion Pharmaceuticals Inc.84 Waterford DriveMarlborough, MA 01752lshao(at)fas.harvard.eduImmediate Past ChairPatrick M. Gordon1 Brae CircleWoburn, MA 01801Patrick.gordon65(at)gmail.comSecretary:Michael SingerSigma-Aldrich3 Strathmore Rd, Natick, MA 01360774-290-1391, michael.singer(at)sial.comTreasurer:James Piper19 Mill Rd, Harvard, MA 01451978-456-3155, piper28(at)attglobal.netAuditor:Anthony RosnerArchivistTim FrigoTrustees:Peter C. Meltzer, Esther A. H. Hopkins,Michael E. StremDirectors-at-LargeDavid Harris, Stephen Lantos, James Phillips,Ralph Scannell, Alfred Viola, John BurkeCouncilors Alternate CouncilorsTerm Ends 12/31/2012Amy E. Tapper Jerry P. JasinskiCatherine E. Costello Gary R. WeismanPatricia A. Mabrouk Norton P. PeetDorothy J. Phillips Edward J. BrushRuth Tanner Michael HurreyTerm Ends 12/31/2013Thomas R. Gilbert Alfred ViolaMichael Singer Sophia R. SuRobert Lichter Kenneth C. MattesMary Shultz Tim FrigoLeland L. Johnson, Jr. Raj (SB) RajurTerm Ends 12/31/2014Katherine Lee Michaeline ChenMichael P. Filosa C. Jaworek-LopesDoris Lewis Jennifer LareseMorton Z. Hoffman Lawrence ScottPatrick Gordon Marietta SchwartzMary Burgess Andrew Scholte

ContentsReport from Bangkok ___________________________________2By Morton Z. Hoffman

Monthly Meeting _______________________________________4At the Holiday Inn Boston-Brookline, Dr. Craig F. Ferris, Center for Transla-tional Neuro-Imaging, Northeastern University, to speak.Title: Functional MRI in Awake Animals: Imaging the Neural Circuitry andPharmacological Control of Aggression, Sex and Fear.

Announcements________________________________________6Call for nominations: The 2012 Theodore William Richards Award for Excellencein Teaching Secondary School Chemistry, Nominations wanted for Aula Laudis.

November Meeting _____________________________________7A report by Kathi Browne and Michael P. Filosa with photos by Morton Z. Hoff-man.

February Historical Events in Chemistry ____________________7By Leopold May, Catholic University of America

Summer Scholar Report _________________________________8Novel Approach to Symmetrical Amino Acid-Derived Peptide IsosteresBy Matthew P. Mower and Craig K. Zercher, University of New Hampshire,Durham, NH

Cape Cod Science Cafe a Success________________________11By Jack Driscoll with photos by Randy Weintraub and Jennifer Maclachlan

2012 Richards Medal to Tobin Jay Marks __________________11

Cover: February speaker, Dr. Craig F. Ferris, Center for Translational Neuro-Imaging, Northeastern University (Photo courtesy of Dr. Ferris).

Deadlines: April 2012 Issue: February 15, 2012May 2012 Issue: March 15, 2012

All Chairs of standingCommittees, the editor of THE NUCLEUS, and the Trustees of SectionFunds are members of theBoard of Directors. AnyCoun cilor of the American Chemical Soci-ety residing within the section area is an exofficio member of the Board of Directors.

90th Anniversary Issue of The NUCLEUS


Monday, February 21, I chose to returnon a very long Saturday in the reversedirection. I was further advised that Icould receive a tourist visa at no costupon arrival and obtain some local cur-rency (approx. 30 baht to $1), and thatno special shots or vaccinations wouldbe necessary as long as travel did notinvolve remote areas outside ofBangkok. I was told to follow theusual travel precautions: drink onlybottled water; don’t eat cut fruit (anexception might be made for doing soat the breakfast buffet in the four-starPathumwan Princess Hotel where wewould be staying); avoid wearing redor yellow shirts, as those have politicalimplications in Thailand.

As it turned out, I would be travel-ing on the same flight from Tokyo toBangkok as another member of theteam, Ms. Anita Romero, an Interna-tional Protocol Officer at Sandia, whowas handling the logistical matters; wearranged to rendezvous at the UnitedClub at Narita Airport (NRT) upon thearrival of her flight from Los Angeles.Inasmuch as she had made many previ-ous trips to Southeast Asia, she wouldserve as a good resource to guide methrough any uncertainties when we gotto Bangkok (BKK). As luck wouldhave it, our flight from NRT to BKKthat Friday night was cancelled due toan electrical malfunction about an hourafter the already weather-delayed flighthad been boarded, the passengers weretold to wait in the United Club toreceive news about their overnightaccommodations and flights on Satur-day. After another hour’s wait, myname was called and I was told toretrieve my luggage, pass throughJapanese customs and immigration, andboard a bus to the hotel in the rapidlyfalling snow, where I could get somesleep and find out about the next step onthe journey. Ms. Romero was assignedto another bus and hotel; I would notsee her again until Monday morning inBangkok. Fortunately, our cell phonesworked and I was able to contact her;she informed the Pathumwan PrincessHotel and the transportation service

that was to pick me up at BKK aboutmy delayed arrival.

My overnight accommodationswould be at the New Otani Hotel inTokyo, a 90-minute bus ride from NRT.Our group arrived at the hotel at 1 a.m.on Saturday, discovered that no infor-mation about the next flight had yetbeen communicated, and checked in; Iremember setting my alarm for 6 a.m.before falling asleep. The phone in theroom rang at 5 a.m. with the news thatthe bus back to NRT would leave before6:30; I was ticketed for a Thai Airwaysflight at 10:45 a.m. with arrival at BKKat 3:45 p.m. The limousine was waitingfor me, and I arrived at the hotel atabout 5 o’clock, ready to sleep!

Although far from bright-eyed andbushy-tailed, I spent a good part ofSunday playing tourist; the weatherwas warm but not overly humid, andthe ferry ride up and down the ChaoPhraya River past the temples andother sights was very pleasant. Thatevening, I met Dr. Ho again and wasintroduced to Dr. Douglas Walters, Co-Director of Chemical Safety at theEnvironmental and Chemical SafetyEducational Institute in Raleigh, NC,who was the leader of the workshop.

The CSSO course was held atChulalongkorn University, where San-dia is in the process of establishing anAsian Regional Center for ChemicalSafety and Security with chemistry pro-fessor Supawan Tantayanon (Ph.D.Worcester Polytechnic Institute), whois the current President of the ChemicalSociety of Thailand and President-electof the Federation of Asian Chemical

Societies (FACS), and served as thehost of the event and a member of theworkshop team. The 27 participants(Thailand: 10; Vietnam: 5; Cambodia:7; Laos: 5) represented academia,industry, and government laboratories,and were chemists of all backgrounds,including environmental engineering.They all were either practicing chemi-cal safety officers or were aspiring tomove in that direction.

In order to help the participantsbring the messages of the workshopback home, the organizers providedthem with a large amount of material:books, brochures, goggles, gloves, anda printout of all the lecture presenta-tions, which were contained in a large,ring-bound volume. As a result, theparticipants had on hand all the infor-mation that was presented orally, ena -bling them to follow along and makenotes during the lectures, which were,of course, in English, their second (orthird) language. Because of the mag-

Corporate Patrons $2000 - or moreAstraZeneca PharmaceuticalsEisai PharmaceuticalsEMD SeronoGenzyme Corp.Johnson MattheyMerck & Co.NovartisPfizer Inc.Schering Corp.Strem Chemicals, Inc.Vertex Pharmaceuticals$1000-$1999Boehringer IngelheimGlaxoSmithKlineIrix PharmaceuticalsLyophilization Services of NESundia MeditechYes Bank$300-$999Cambridge Major LabsGirindusMerrimack ConsultantsOrganixPCI SynthesisSigma AldrichWaters Corp.Wilmington PharmaTech

continued on page 13

Report from Bangkokcontinued from page 2

(l-r) Douglas Walters (Environmental andChemical Safety Educational Institute), PaulineHo (Sandia National Laboratories), SupawanTantayanon (Chulalongkorn University), AnitaRomero (Sandia National Laboratories), Mor-ton Hoffman (Boston University).


BiographyCraig F. Ferris is the Professor of Psy-chology and Pharmaceutical Sciences,Director, Center for Translational Neuro -Imaging, North-eastern University,Boston MA. Dr. Ferris received hisB.S. at the University of Massachusettsand his Ph.D. in physiology at the NewYork Medical College. He was a post-doctoral fellow in neuroendocrinologyat Harvard Medical School. Formerlyhe was Professor of Psychiatry andPhysiology, Director, Center for Com-parative Neuroimaging, University ofMassachusetts Medical School.

He is co-founder, Chief of Biolog-ical Sciences, Azevan Pharmaceuticals,Bethlehem, PA; co-founder, CEO,Insight Neuroimaging Systems, LLC,Worcester, MA; and co-founder, CSO,Ekam Imaging, Inc., Shrewsbury, MA.He has six issued patents and in 30years of academic research, 136 peer-reviewed publications.

His academic research focuses ondevelopmental behavioral neuro-science with a comparative approachstudying a variety of animals, includinghamsters, rats, and monkeys. Interestsinclude the plasticity of the brain andhow early emotional and environmen-

AbstractFunctional magnetic resonance imag-ing (fMRI) in awake animals is a win-dow on the brain, allowing behavioralneuroscientists the ability to image thebrain activity associated with highlyemotional behaviors like aggression,sex and fear. With fMRI in awake ani-mals, it is possible to resolve patternsof neuronal activity across the entirebrain with high spatial and temporalresolution. Synchronized changes inneuronal activity across multiple brainareas can be viewed as functional neu-roanatomical circuits coordinating thethoughts, memories and emotions forparticular behaviors. To this end,fMRI in conscious rats combined with3D computational analysis was used toidentifying the putative distributedneural circuits involved in aggressive

Monthly MeetingThe 921st Meeting of the Northeastern Section of the AmericanChemical SocietyThursday, February 9th, 2012Holiday Inn Boston – Brookline1200 Beacon Street, Brookline, MA 02446

4:30 pm Board Meeting

5:30 pm Social Hour

6:30 pm Dinner

7:30 pm Welcome Dr. Ruth Tanner, Chair, NESACS

Speaker Dr. Craig F. Ferris, Center for Translational Neuro-Imaging,Northeastern UniversityFunctional MRI in Awake Animals: Imaging the Neural Circuitryand Pharmacological Control of Aggression, Sex, and Fear

Dinner reservations should be made no later than 12:00 noon, Friday, February10th. Reservations are to be made using PayPal services: http://acssympo-sium.com/paypal.html. Select pay with credit or debit card option and followthe additional instructions on the page. Members, $30; Non-members, $35;Retirees, $20; Students, $10, Unemployed $10. Reservations for new mem-bers and for additional information, contact the secretary, Anna Singer, between9am and 9pm at (phone/fax 781-272-1966) or [email protected]. Reserva-tions not canceled at least 24 hours in advance must be paid.THE PUBLIC IS INVITEDDirections:From the Mass Pike East/Route 90: Take the Mass Pike East to exit 18, Allston/Cambridge, the exit will be on theleft. Bear right, following signs towards Cambridge. Turn right onto StorrowDrive. Follow Storrow Drive to the Boston University exit. Off the exit followCarlton Street approximately one block to Commonwealth Avenue and turnright. Follow Commonwealth Avenue west and turn left at the second trafficlight onto Saint Paul Street. The hotel is six blocks down on the left, on the cor-ner of Beacon Street and Saint Paul StreetFrom 93 North or South:Take Exit 26, Storrow Drive. Follow Storrow Drive to the Kenmore Square exit,the exit will be on the left. Off the exit, turn right at the first light onto BeaconSt. The hotel is one mile up on the right at 1200 Beacon St. By Public Transportation:The Holiday Inn is conveniently located at the Green C Line “St. Paul Street” TStop.Parking:Meter parking is available on Beacon Street as well as Holiday Inn garage park-ing (It is $6 for unlimited parking. Guests can pick up a voucher from the hoteland pay when they leave.) u



Nominations wanted for Aula LaudisStarting in 1985, the Northeastern Sec-tion has annually honored secondaryschool chemistry teachers in our regionby selecting several for induction intothe Aula Laudis honor society.

Selection is recognition of excel-lence in the teaching of chemistry at thehigh school level. This recognition isbased on both qualitative and quantita-tive criteria that involve the totality ofan individual’s participation in and con-tribution to the teaching profession. In -asmuch as teaching is a skillful art witha wide range of marks of excellence, noone criterion for selection to AulaLaudis is sufficient and no one criterionis necessary. The following criteria, intheir broadest sense, shall be consid-ered by the Selection Committee:• Having taught chemistry to students,

who have won state-wide, regional,or national chemistry competitions,such as the Avery-Ashdown Exami-nation award.

• Having received awards for excel-lence in teaching from state-wide,regional, or national competitions,such as the Presidential Award orNEACT’s Timm Award.

• Having advanced the scholarship ofchemical education, including cur-riculum design, laboratory develop-ment, and the introduction ofpedagogical techniques through pub-lication in recognized education jour-nals and/or presentations at scientificmeetings or continuing educationsymposia.

• Having served as an advisor of extra-curricula activities, such as clubs, sci-ence programs, and science talentsearches, in which the interest ofchemistry students in the subject isadvanced and developed.

• Having performed special service tothe chemical education community,such as through organization of con-tinuing education symposia in chem-istry or web-based bulletin boards.

• Having demonstrated excellence inclassroom teaching as evidencedfrom written in-class evaluations bysupervisors.

• Having had a significant personalimpact on students as evidenced byletters from alumni/ae on behalf ofthe nominee.

• Having provided many years of suc-cessful service in the chemistry class-room, with some of the aboveaccomplishments cited.

The criteria for each final selecteeshall be recorded in its minutes, andshared with the NESACS chair ifdesired.

The selection committee is happyto accept nominations on behalf ofactive and retired secondary schoolchemistry teachers. The length ofteaching service is not a criterion. Nominations, including a half-sheet orlonger summary of accomplishments,may be sent to by March 31, 2012 to: Harvey Gendreau188 Eaton RoadFramingham, MA [email protected] u


The 2012 Theodore WilliamRichards Award for Excellencein Teaching Secondary SchoolChemistryThe Richards Award is the most presti-gious award for high-school chemistryteaching awarded by the NortheasternSection of the American ChemicalSociety. The award is in recognition ofoutstanding, innovative, and inspiredteaching at the secondary level. It isintended to honor a teacher in theNortheastern Section who, throughinnovation and dedication, has inspiredpotential chemists, has communicatedchemistry to non-chemists, or hasinfluenced other teachers of chemistry.

The criteria for excellence corre-spond broadly to the effectiveness withwhich the teacher conveys chemistry,the innovative techniques used to helpstudents comprehend chemical con-cepts, his/her interaction with students,both academic and extra-curricular,and the influence a teacher has had onother teachers for promoting newapproaches to teaching and learning.

The selected teacher will be offi-cially honored and will receive both a$1,500 prize and a Certificate ofRecognition at the NESACS HighSchool Night ceremony in May 2012.

A complete description of theaward, the nomination criteria, andnomination forms can be obtainedfrom the NESACS website at:<http://www.nesacs.org/awards_richards.html> Nominations are due no laterthan April 15, 2012 to the RichardsAward Committee, attn: Steve Lantos,[email protected] (orvia US Mail to: Steve Lantos, Sci.Dept. Brookline HS, 115 GreenoughSt, Brookline MA 02445) u

Announcements

Q. Exactly, how many awards andscholarships does NESACS sponsor?

A) One b) Two c) Many

www.nesacs.org/awards

http://www.nesacs.org/awards_info.html


Norris Award DinnerDr. Peter Mahaffy of the King’s Uni-versity College in Edmonton, Canada,received the 60th annual James FlackNorris Award for OutstandingAchieve ment in Teaching Chemistry atthe November meeting of theNESACS, held on November 10th atAstra-Zeneca in Waltham, Massachu-setts. Dr. Mahaffy was introduced byhis associate, Dr. Margaret-AnnArmour, of the University of Alberta.

Dr. Mahaffy’s presentation, ShouldAtoms Come First? Teaching Chemis -try from Rich Contexts, addressed waysin which the current general chem istrycurriculum could be restructured toensure a curriculum rich in contentwhile simultaneously addressing thecurrent challenges faced by scientistswithin the global community.

Dr. Mahaffy has generously donat -ed the honorarium received from theaward to support African chemistryeducation and undergraduate studentresearch experiences. (By KathiBrowne)

Heyn Memorial PrizeAt the November Meeting the ArnoHeyn Memorial Book Prize was alsopresented to Harvey Steiner of ArtRelated Technology, Inc. Harvey rem-inisced about the day Arno came inwith “his muscle, Vince Gale” andasked Harvey, “Can you do this?” Thatbegan Harvey’s 20 year tenure produc-ing 10 issues per year of the Nucleus.Harvey marveled at Arno’s memory ofdetail and his visits with “his posse ofMyke Simon and Don Rickter” (alsono slouches at attention to detail) toproofread and correct the final copy.Vince, Myke and Don are all previousrecipients of the Heyn Prize. Harveywas a gracious and most appropriaterecipient of the seventh award.

AstraZeneca was a wonderfulvenue for the monthly meeting. Manythanks to Ken Mattes and Astra- Zeneca for making this possible.(By Michael Filosa) u

November Meeting

Peter Mahaffy with Margaret-Ann Armour (Uni-versity of Alberta, Canada)

Peter Mahaffy with his wife, Cheryl.

Peter Mahaffy flanked by members of the NorrisAward Committee: Kathleen Browne (2011Chair), at right, and Mary Jane Shultz, (2010chair)

All photos by Morton Z. Hoffman

Members of the NESACS Board of Publicationswith Harvey Steiner (Art Related Technology),recipient of the 2011 Arno Heyn Memorial BookPrize: (l-r) Mary Mahaney, Chair; Vivian Wal-worth, Past-chair; Mr. Steiner; Myron Simon,Associate Editor of the Nucleus; MichaelFilosa, Editor of the Nucleus.

February 1, 1905Born on this date, Emilio Segré,with C. Perrier, discovered tech-netium (Tc, 43). In 1940, togetherwiith D. R. Corson and K. R.MacKenzie, he co-discovered asta-tine (At, 85). He demonstrated theantiproton in 1955. He shared theNobel Prize in Physics (1959) withOwen Chamberlain for their discov-ery of the antiproton.

February 7, 1905Ulf von Euler, who was born on thisdate, shared the Nobel Prize in Med-icine or Physiology in 1970 with J.Axelrod and B. Katz for discoveriesconcerning humoral transmitters inthe nerve terminals and the mecha-nism for their storage, release andinactivation.

February 9, 1871Edward C. C. Baly, who was bornon this date, showed that sugar andother organic compounds are formedfrom water, carbon dioxide, andammonia under the influence oflight.

February 9, 1950Californium was discovered by ionexchange chromatography on thisdate at the University of California,Berkeley.

February 11, 1914Alwin Mittasch and ChristianSchneider filed application resultingin US Patent 1,201,850, describingcatalytic production of methanolfrom carbon monoxide & hydrogen.

February Historical EventsIn Chemistryby Leopold May, The Catholic University of America, Washington, DC



Abstract Mimicry of biological peptides through isosteric

replacement of the amide linkage has been demonstrated toinhibit activity of enzymes including the HIV aspartyl pro-tease, whose functions are essential for propagation of thevirus. Currently reported peptide mimics lack either therestricted rotation or hydrogen bonding capability of theamide bond and thus suffer from decreased efficacy.Methodology developed within the Zercher group allowsefficient access to cyclopropanol isosteres that are expectedto exhibit uncompromised mimicry of natural peptides.Cyclopropanol isosteres were accessed from amino acid-derived diketones, which were prepared using a Lewis acid-assisted mixed Claisen reaction. Proline andphenylalanine-derived systems were investigated with thedesired proline-derived cyclopropanol isolated in moderateyield. Investigation of phenylalanine-containing systems iscurrently under way, as is investigation of a novel intramol-ecular rearrangement of these cyclopropanols. Background

Through hydrolytic cleavage of an amide linkage, theHIV aspartyl protease provides peptide fragments necessaryfor viral propagation.1 Isosteric replacement of the amidefunctionality with a functionality resistant to hydrolysis,such as a ketomethylene or hydroxyethylene unit, hasserved as inspiration in the design of successful proteaseinhibitors.1 Preparation of these isosteres, however, can belengthy and without fine stereocontrol.2,3 Furthermore, freerotation around these amide replacements decreases theirinhibitory efficacy.4 This led to development of cyclopropyland alkenyl isosteres, which exhibited rigid structures remi-niscent of the amide bond, but also sacrificed mimicry of thehydrogen bonding ability.4 Methodology developed recentlywithin the Zercher group provides efficient access to aunique and otherwise unreported class of isosteres replacingthe amide bond with a cyclopropanol moiety.5 This cyclo-propanol provides the desired rigidity, while also maintain-ing hydrogen bonding capability and mimicking thegeometry of the tetrahedral intermediate formed duringamide hydrolysis (Fig. 1).

Exposure of the appropriate β-dicarbonyl-containingcompound to a bis(iodomethyl)zinc carbenoid, similar to theFurukawa-modified Simmons-Smith carbenoid, results inhomologation of the carbon backbone followed by cyclo-propanation to give the cyclopropanol isostere in a one ves-sel reaction.5 When considering potential enzyme inhibitorsto be targeted through this methodology, the C2 symmetricnature of the HIV aspartyl protease indicates that a symmet-ric or psuedosymmetric substrate may have strong selectiv-ity and potency.6 This was confirmed by Kempf andco-workers who prepared a large library of C2 symmetrichydroxyethylene isosteres and found many of them to havesub-nanomolar IC50’s.7 With this in mind, we are developingthe homologation-cyclopropanation of a novel class of sym-metrical amino acid-derived β-diketones 1 to form pseu-dosymmetric cyclopropanol peptide isosteres 2 (Scheme 1).

Preparation of β-Diketone Precursors Preparation of amino acid-derived β-diketones was

envisioned through a mixed Claisen condensation of aketone with some form of activated ester. Many differentactivated esters and enolate forming conditions wereattempted before two successful methods were identified.The first step in preparation of the ketone and activated ester

Summer Scholar ReportNovel approach to symmetrical amino acid-derived peptide isosteresMatthew P. Mower and Charles K. Zercher*, University of New Hampshire, Durham, NH

Scheme 1 – Amino acid-derived cyclopropanol isosteresfrom novel β-diketones

Scheme 2 – Preparation of amino acid-derived ketone 5Fig. 1 – Unique cyclopropanol isostere

was N-protection of the amino acid to prevent quenching ofan intermediate enolate formed during the homologation-cyclopropanation reaction. Due to its ease of handling andprotection, L-proline was chosen as the model system withwhich to optimize β-diketone and cyclopropanol formingconditions. L-Proline was protected as the sulfonamide 3,then subjected to a DCC-facilitated coupling reaction withMeldrum’s acid to form the adduct 4. Hydrolysis of thisadduct and flash chromatography of the crude mixture gavethe ketone 5 (Scheme 2).

Tosyl protected proline (3) was also reacted withthionyl chloride and 1H-benzotriazole to form the activatedspecies 6, which was condensed with ketone 5 in a Lewisacid-assisted mixed Claisen reaction to form the desired β-diketone 7 (Scheme 3). Recrystallization of the crude mix-ture from ethanol provided analytical grade β-diketone.

β-Diketone 7 was also prepared through a more tradi-tional mixed Claisen reaction, using lithium diisopropy-lamide at -78 °C to form the enolate of 5, which was thenreacted with active species 6. This procedure resulted inpoorer yields of the desired product and a crude mixture thatwas not amenable to recrystallization. Through 1H NMRanalysis, it was observed that β-diketone 7 exists predomi-nantly in its enol form, with the exact ratio of enol to ketospecies differing slightly with concentration. The presenceof a single resonance for the enol form’s sp2 CH moiety sug-gests that this material was prepared with negligible epimer-ization, barring isochronicity of the two diastereomers.

The phenylalanine-derived analog of β-diketone 7 wasalso prepared using similar methodology. Protection as the

phthalimide 8 followed by Meldrum’s acid coupling andexposure to modified mixed Claisen conditions gave the β-diketone 9 (Scheme 4), though in poorer yield than the pro-line-derived system, and in a crude mixture which requiredflash chromatography to separate. Unfortunately, 1H NMRanalysis of the purified material revealed two different reso-nances from the enol form of 9, indicating that epimeriza-tion of the phenylalanine residue had occurred at some pointduring the preparation.

To investigate this epimerization, the Meldrum’s acidadduct 10 was opened with the chiral alcohol (R)-2-butanol,forming β-keto ester 11 (Scheme 5) in what an initial analy-sis indicates to be a mixture of diastereomers. This suggeststhat the material leading into the mixed Claisen step hasalready been epimerized, and appropriate steps are currentlybeing taken to determine exactly when the epimerizationoccurred.

Preparation of Cyclopropanol Isosteres L-Proline-derived β-diketone 7 was exposed to the

bis(iodomethyl)zinc carbenoid at 0 °C and a crude mixturecontaining many different products was obtained. Afterchromatographic separation of the crude mixture, minoramounts of a diastereomeric mixture of desired cyclo-propanol 12 were obtained, as well as methyl sulfone 13 andother unidentified products (Scheme 6). Sulfone 13 isbelieved to be formed through elimination of p-toluenesulfi-nate from one of the proline residues, followed by methyla-tion of this species by the zinc carbenoid.

In order to limit the formation of sulfone 13, it was nec-


Continued on page 10

Summer Scholarcontinued from page 8

Scheme 3 – Mixed Claisen to form β-diketone 7

Scheme 4 – Preparation of phenylalanine derived β-dike-tone 9

Scheme 5 – Opening of phenylalanine Meldrum’s acidadduct with chiral alcohol

Scheme 6 – Initial homologation-cyclopropanation of β-diketone 7Figure 2 – 1H NMR expansion of enol and keto forms of β-

diketone 7


essary to know whether the sulfone was formed as a decom-position product of some intermediate species, or through anundesired reaction of the starting material itself with zinccarbenoid. The first step of homologation-cyclopropanationinvolves deprotonation of the β-diketone and formation of azinc stabilized enolate. If a species analogous to β-diketone7 but incapable of forming an enolate could be prepared,then reaction of this species with zinc carbenoid wouldreveal whether loss of the tosyl protecting group occurredbefore homologation-cyclopropanation or sometime afterthis process began. Thus, β-diketone 7 was modified as thegem-dimethyl compound 14 and subjected to homologation-cyclopropanation conditions, resulting in no reaction(Scheme 7).

This indicated to us that loss of the tosyl protectinggroup was likely due to the high reactivity of one or morereaction intermediates. Strong evidence exists to suggestthat the homologation-cyclopropanation reaction proceedsthrough a series of zinc stabilized enolates and homoeno-lates.8,9 It was hypothesized that introduction of a reagent totrap these species may diminish formation of unwantedbyproducts during the homologation-cyclopropanation reac-tion. Exposure of β-diketone 7 to homologation-cyclopropa-nation conditions in the presence of trimethylsilylchloride(TMS-Cl) followed by selective removal of the silyl groupresulted in a much cleaner crude reaction mixture with for-mation of cyclopropanol 12 in >50% yields. Sulfone 13 andat least one other byproduct were still present, though indecreased amounts.

An interesting consequence of introducing TMS-Cl tothe reaction mixture was an increase of the diastereomericratio in which cyclopropanol 12 was observed. When stan-dard homologation-cyclopropanation conditions were used,a roughly one to one mixture of diastereomers wasobserved. When the zinc carbenoid reaction is performed inthe presence of TMS-Cl, however, diastereomeric ratios ofapproximately 1:4 were observed. We believe this is due toTMS protection of the cyclopropanol, which minimizes thepossibility of interconversion between diastereomers. Inves-tigation of the formation and reactivity of β-diketonederived cyclopropanols 15 and 16 revealed a unique iso-meric interconversion when exposed to bis(iodomethyl)zinccarbenoid (Scheme 8).

This rearrangement is hypothesized to proceed throughfragmentation of the cyclopropane with concurrent nucle-ophilic attack of the ketone functionality. If zinc were to becomplexed between the Lewis basic oxygens, rearrange-ment through this conformation would be predicted to resultin the interconversion of diastereomers. Therefore, by pro-tecting the cyclopropanol moiety as it is formed with TMS,this mechanistic pathway is shut down, no rearrangement isallowed to occur, and the cyclopropanol product is formedwith greater diastereoselectivity. To further investigate thistheory, the TMS-protected analog of cyclopropanol 12 wasisolated and heated at 200 °C in a closed vessel under inertatmosphere for one hour, resulting in no change of thediastereomeric ratio as observed via 1H NMR.

Phenylalanine derived β-diketone 9 has also beenexposed to homologation-cyclopropanation conditions, bothin the presence and absence of TMS-Cl, and initial NMRanalysis of the crude mixtures indicates formation of poten-tial product material. Future Work

Epimerization during the formation of phenylalaninederived β-diketone 9 is an issue needing a solution. Recentresults have suggested where stereochemical integrity islost, and optimization of the synthetic route will be under-taken to minimize epimerization.

Optimization studies of cyclopropanol- forming condi-tions are also underway. Recent results indicate that coolingthe reaction vessel to 0 °C for the entirety of the reactionmay further decrease formation of sulfone 13 and otherbyproducts, as well as increase the diastereoselectivity ofthe reaction. Controlled rearrangement of the cyclopropanolisomers is also being attempted in an effort to identify thethermodynamic characteristics of the rearrangement. Acknowledgements

Matthew Mower was funded by a Norris-Richards sum-mer scholarship given by the NESACS. He would like tothank Dr. Charles Zercher for his insightful guidance, aswell as the current and past members of the Zercher group.Special thanks are extended to Dr. Ian Taschner, who pro-vided the seminal idea for this project. 1 Mastrolorenzo, A.; Rusconi, S.; Scozzafava, A.; Barbaro,

G.; Supruan, C.T. Curr. Med Chem. 2007, 14, 2734 – 2748.2 Harberson, S. L. Rich, D. H. J. Med. Chem. 1989, 32, 1378

– 1392.3 Ballini, R.; Bosica, G.; Gigli, F. Tetrahedron 1998, 54,

7573 – 7580.4 Chen, C.; Sieburth, S.; Glekas, A.; Hewitt, G. W.; Trainor,

G. L.; Erickson-Viitanen, S.; Garber, S. S.; Cordova, B.;Jeffry, S.; Klabe, R. M. Chemistry and Biology 2001, 12,1161 – 1166.


Scheme 7 – Preparation and exposure of dimethyl β-dike-tone 14 to zinc carbenoid

Scheme 8 – Interconversion of cyclopropanol isomers


Tobin Marksto receive2012TheodoreWilliamsRichardsMedalProfessor Tobin Jay Marks, the CharlesE. & Emma H. Morrison Professor ofChemistry, Vladimir N. Ipatieff Profes-sor of Catalytic Chemistry, and Profes-sor of Materials Science andEngin eering, at Northwestern Univer-sity, has been selected to receive the2012 Theodore William RichardsMedal Award for “conspicuousachieve ment in chemistry.” TheRichards Medal, first presented in1932, is awarded every two years by

The Cape Cod Science Café was heldat the Sandwich Public Library from 1-3 pm on Sunday December 11, 2011.Flyers were printed up and distributedthrough the Sandwich & BarnstableSchools, and articles were printed inthe Sandwich Enterprise (http://bit.ly/uSoQ68 ) and the Cape Cod Times(http://bit.ly/uTk5HX ). The responsewas tremendous. About 150 peopleattended .

The library phone was very busySunday morning. Everyone wasexcited as students and parents waitedin lines 3-4 deep to watch the experi-ments. The publicity for the event wasfocused on Sandwich and Barnstable,yet we had children from Weymouthand Hingham in attendance. A gradeschool principal from Plymouth whothought that her students might beinterested in this event visited us also.At least three parents said that theirdaughters insisted that their parentstake them because they were interestedin science. The children were veryexcited, and I found that even a 3.5year old girl was able to determine thepH of solutions by matching the colorson the pH paper.

The article in the Cape Cod Timesdrew a 55-year member of the ACSfrom Sandwich to our meeting. Upuntil now, he has not been connected toour local section. He saw the article inthe Enterprise Newspapers! We aredelighted to welcome him to NESACS,and he plans to volunteer at our nextK-12 outreach event. u


Cape Cod Science Café aSuccessBy Jack Driscoll (excerpted from the PID Analyzer blog: The Analyzer Sourcehttp://analyzersource.blogspot.com/2011/12

Using chemicals to teach students about bloodtypes. (Paul Reibach, NESACS member). Asummary of this new experiment on blood typingdrew a great deal of interest from the students(http://bit.ly/tKadQJ )

(Photo courtesy of Randy Weintraub)

Healthy foodand of coursean Internationalyear of chem-istry Cake (thefood and cakewere preparedby Marshland)was available.

(Photo courtesy of Jennifer Maclachlan)

We had many chemistry Ambassador helpers atour event. Go chemistry ambassadors!

(Photo courtesy of Jennifer Maclachlan)



motivation, sexual motivation and con-ditioned predatory fear and how theseneural circuits are affected by drugsaltering vasopressin and serotonin neu-rotransmission.

Data will be presented showingchanges in brain activity associatedwith aggressive motivation. Sociallydominant male rats can be positionedin the MR scanner and their brainimaged in response to the presentationof a strange dominant male. The subse-quent change in brain activity reflectsaggressive motivation toward theintruder and shows a robust pattern ofactivation in the thalamus, cortex andhypothalamus similar to that precedinga generalized seizure. When a drug isgiven to block vasopressin receptors orincrease serotonin neurotransmission,aggressive motivation is suppressedalong with the increase in brain activ-ity. Interestingly, in the presence ofvasopressin receptor blockade and sup-pressed aggression, dominant malesstill show sexual motivation andheightened brain activity toward sexu-ally receptive females. In contrast, flu-oxetine, a selective serotonin reuptakeinhibitor, reduces aggressive respond-ing but impairs sexual behavior.

Data will be presented on a newlydeveloped, unique model of predatoryfear conditioning using a live sable fer-ret as the unconditioned stimulus. Inshort, rats exposed to a ferret whileexperiencing the taste of sucrose showa dramatic increase in brain activity inthe limbic cortex and hippocampusweeks later in response to the taste ofsucrose alone. Indeed the brain activityassociated with the memory is fargreater than the initial exposure to thepredator. Treatment with an orallyactive vasopressin receptor antagonistblocks the sucrose-associated trau-matic memory but not the initial innatefear response. u

Abstractcontinued from page 5

tal risk factors alter social and cogni-tive behaviors. Risk factors includedrugs of abuse like cocaine and alcohol,and social subjugation in the context ofdominant/subordinate relationships.

His laboratory uses standardmolecular and neurobiological tech-niques to study the brains of rodents.In addition, ultra-high field magneticresonance imaging is used as a non-invasive tool for developmental studiesin monkeys, enabling one to followchanges in brain structure, chemistry,and function in the same animal overthe course of its life. The goal of thisresearch is to better understand thebrain mechanisms contributing to men-tal illness and drug addiction in thehope of improving psychosocial andpsycho-pharmacologic interventionstrategies. u

Biographycontinued from page 5

5 Lin, W.; Theberge, C. R.; Henderson,T. J.; Zercher, C. K.; Jasinski, J. P.;Butcher, R. J. J. Org. Chem. 2009, 74,645 – 651.

6 Kuo, Lawrence C.; Shafer, Jules A.Retroviral Proteases. AcademicPress, 1994. 334 – 335.

7 Kempf, D. J.; Codacovi, L.; Wang, X.C.; Kohlbrenner, W. E.; Wideburg, N.E.; Saldivar, A.; Vasa-vanonda, S.;Marsh, K. C.; Bryant, P.; Sham, H. L.;Green, B. E.; Betebenner, D. A.;Erickson, J.; Norbeck, D. W. J. Med.Chem.1993, 36, 320 – 30.

8 Brogan, J. B.; Zercher, C. K. J. Org.Chem. 1997, 62, 6444 – 6446.

9 Eger, W. A.; Zercher, C. K.; Williams,C. M. J. Org. Chem. 2010, 75, 7322 –7331. u


February 14, 1878Father Julius Nieuland, who wasknown as the “Father of AcetyleneChemistry,” was born on this date.He is a discoverer of neoprene andwas the first Ph.D. in Chemistryfrom Catholic University in 1905.

February 15, 1873Hans K. A. S. von Euler-Chelpin, aresearcher on enzymes and fermen-tation, was born on this date. Heshared the Nobel Prize in 1929 withArthur Harden for their investiga-tions on the fermentation of sugarand fermentative enzymes. He wasborn and this day

February 19, 1955 One atom of mendelevium (Md,101) was produced by the bombard-ment of one billion atoms of 253Eson this date.

February 20, 1937Robert Huber, a researcher on thethree-dimensional structure of pro-teins involved in photosynthesis,was born on this date. In 1988 heshared the Nobel Prize in Chemistrywith Johann Deisenhofer and Hart-mut Michel for the determination ofthe three-dimensional structure of aphotosynthetic reaction centre.

February 25.1898Seventy-five years ago WilliamThomas Astbury used X-ray diffrac-tion patterns to study the structuresof nucleic acids and wool in both thestretched and unstretched forms. Hewas born on this date.

February 27, 1901 Fifty years ago Linus C. Pauling

was awarded the Nobel Peace Prize.He was born on this date. He was aresearcher on structure of molecules,valency, and resonance. He receivedthe Nobel Prize in Chemistry in1954 for his research into the natureof the chemical bond and its applica-tion to the elucidation of the struc-ture of complex substances.

Additional historical events can befound at Dr. May’s website, http://fac-ulty.cua.edu/may/Chemistrycalendar.htm. u

Historical Eventscontinued from page 7

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nitude of the material to be covered inthe time that was available, the lecturesby Drs. Ho and Walters moved alongat an almost unrelenting pace, espe-cially during the first two days; ineffect, the participants did not activelyparticipate, which could also be due tocultural factors, English-language ver-bal abilities, or personal reticence.

The interactions among the partic-ipants and with the members of theteam changed dramatically on Wednes-day morning, when the group left thelecture room and went to a generalchemistry lab, where a safety inspec-tion walk-through was performed, thecleanup of liquid and solid spills wasdemonstrated, and a small laboratorykit was displayed by Professor Tanta-yanon. Back in the lecture room, theparticipants spoke about the primaryproblems at their institutions and theengineering controls that were needed,which had been their overnight home-work assignment. Among the issuesreported by participants were lack ofventilation; inadequate chemical wastedisposal and storage; faulty electricalequipment; getting students (both grad-uate and undergraduates) to wearproper safety glasses and shoes, and tofollow the safety rules; proper manage-ment of gas cylinders; getting theattention of faculty colleagues.

On Thursday morning, the demon-stration of fire alarms and smoke detec-tors by a fire control officer and thesubsequent outdoors hands-on activity

with oil and liquefied gas fires werevery effective; I doubt that anyone willquickly forget the latter! Later on thatday, the participants discussed theirovernight homework on the specificsafety issues at their facilities. By thetime the samples of personal protectiveequipment were distributed that after-noon, the atmosphere had becomeextremely friendly and collegial.

On Friday morning, I met with theparticipants in two groups for a littlemore than an hour each to discuss thecase study of the fatal laboratory fire atUCLA in December 2008, which hadbeen assigned for overnight home-work; the other group went to the labto practice inspection and spillcleanup. Later, the participants gath-ered in national groups to discuss whatmight be the next steps to take towardchemical safety and security withineach country, and to report back orallyto everyone. The plans that wereexpressed to form national networks,and the invitation from Vietnam for avisit from the Chemical SecurityEngagement Program to provide train-ing, were very positive outcomes.

By the end of the farewell dinneron Friday evening, the atmosphere wasrich with friendship, happiness, and thebitter sweet sadness of leave-taking. Itwas clear to me that the event was agreat success with respect to the thor-ough development and presentation ofthe content, the deep care in the prepa-rations for the trip, and the sensitiveattention to details on the ground inBangkok on the part of the organizingteam. u

Report from Bangkokcontinued from page 4

D I R E C T O R Y

SERVICES

Morton Z. Hoffman, Boston University professor emeritus and IUPAC Representative, with attendeesof the Chemical Safety and Security Officer (CSSO) workshop held in Bangkok, Thailand. Attendeeswere academic and laboratory chemists from the Mekong Delta region (Cambodia, Laos, Vietman).


B U S I N E S S D I R E C T O R Y

SERVICESSERVICESSERVICES


CAREER SERVICESSERVICES

B U S I N E S S D I R E C T O R Y

SERVICES

Index of AdvertisersCreaGen Biosciences ..........13Drew University ....................6Eastern Scientific Co. ..........11EMD Chemicals, Inc. ............2Front Run OrganX, Inc........14Huffman Laboratories, Inc. .14Mass-Vac, Inc. .....................16Micron Inc. ..........................14Nacalai USA, Inc.................13New Era Enterprises, Inc.....14NuMega Resonance Labs....14Organix, Inc.........................14PCI Synthesis ......................15PolyOrg, Inc. .......................15Rilas Technologies, Inc. ......14Robertson Microlit Labs. ....14Vacuubrand, Inc...................15Waters Corporation .............15

Check the NESACS home pagefor late Calendar additions:http://www.NESACS.orgNote also the Chemistry Department webpages for travel directions and updates.These include:http://chemserv.bc.edu/seminar.htmlhttp://www.bu.edu/chemistry/events/http://www.chem.brandeis.edu/colloquium.shtmlhttp://www-chem.harvard.edu/events/http://web.mit.edu/chemistry/www.chem.neu.edu/web/calendar/index.htmlhttp://chem.tufts.edu/seminars.html [CHEM.]http://ase.tufts.edu/chemical/seminar.htm

[CHEM. ENGG.]http://www.chem.umb.edu/www.umassd.edu/cas/chemistry/seminars.cfmwww.uml.edu/Dept/Chemistry/speakers.htmlhttp://www.unh.edu/chemistry/seminars.html

Feb 01Prof. Kenichiro Itami,(Nagoya Univ.)Boston College, Merkert 1304:00 pm

Feb 02 Kenichiro Itami (Nagoya Univ.)Novartis Lecture in Organic ChemistryMIT 6-120 4:00 pm

Feb 07 Ulrich Kortz (Jacobs University, Germany)“The Noble Chemistry of Polyoxometalates”MIT, 6-120 4:15pm

Feb 08 David Giedroc (Indiana Univ.) MIT, 6-120 4:15 pm

Feb 09Abbott Lecture in Organic ChemistryGary A. Molander (U. Pennsylvania) Michael J. Rozema (Abbott)MIT, 6-120 4:00pmProf. William Miller (UC Berkeley)Harvard University, Pfizer Hall4:30pm

Feb 16Prof. Stephen Leone (UC, Berkeley)MIT 6-120 4:30 pm

Feb 29Clark Landis (Univ. Wisconsin – Madison)Harvard University, Pfizer Lecture Hall4:15pm

Notices for The NucleusCalendar of Seminars should be sent to:Sheila E Rodman Konarka Technologies, Inc.116 John St. Suite 12, Lowell, MA 01852 email: srodman(at)konarka.com u

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Calendarthe Northeastern Section of the Ameri-can Chemical Society. The award,which includes gold and silver medals,will be presented to Professor Marks onThursday March 8, 2012 at HarvardUniversity. Marks’s research activitieshave spanned the fields of inorganicchemistry, organometallic chemistry,and materials science, resulting inapproximately 1030 publications (h-index 116). His contributions havebeen diverse and include the develop-ment of new catalytic polymerizationprocesses for polyolefins and function-alized polyolefins, ring-opening Zieglerpolymerization, and silanolytic chaintransfer, as well as the exploitation oforgano-f-element catalysts to affectstereoselective hydro-functionalization,the rational design of environmentallystable organic n-type semiconductorsand self-assembled nanodielectrics forprinted electronics, and the use ofvolatile metal-organic precursors toaffect the rational growth of supercon-ductor, oxide dielectric, and transparentconducting oxide thin films. Prof.Marks was the recipient of the NationalMedal of Science in 2005. He is a fel-low of the National Academy of Sci-ences and the American Academy ofArts and Sciences. He has mentoredover 120 PhD students and nearly asmany postdoctoral fellows, with morethan 110 currently holding tenure-lineacademic positions worldwide. u

Tobin Markscontinued from page 11

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Documents

Jan 2011 NUCLEUS AA2B - Welcome to NESACS - … The Nucleus February 2012 Monday, February 21, I chose to return on a very long Saturday in the reverse direction. I was further advised