Chapter 8. Synthetic Receptors for Amino Acids and Peptides Debrabata Maity and Carsten Schmuck*...
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Chapter 8. Synthetic Receptors for Amino Acids and Peptides Debrabata Maity and Carsten Schmuck* University of Duisburg-Essen, Faculty of Chemistry, Universitätsstrasse
Chapter 8. Synthetic Receptors for Amino Acids and Peptides
Debrabata Maity and Carsten Schmuck* University of Duisburg-Essen,
Faculty of Chemistry, Universittsstrasse 7, 45141 Essen, Germany
*Email: [email protected] Supplementary information for
Synthetic Receptors for Biomolecules: Design Principles and
Applications The Royal Society of Chemistry 2015
Slide 2
Figure 8.1 Schematic of the binding of glutamate (green) in a
G-protein coupled glutamate receptor with red lines showing
H-bonding and blue lines showing van der Waal contacts. (Reproduced
with permission from Br. J. Clin. Pharmacol., 2009, 156, 869, 2009
British Pharmacological Society) Supplementary information for
Synthetic Receptors for Biomolecules: Design Principles and
Applications The Royal Society of Chemistry 2015
Slide 3
Figure 8.2 Model of the binding interaction between the RGD
peptide (Arg-Gly-Asp) and binding site of v 3 - integrin. - and
-Integrin subunits are represented in pink and pale cyan,
respectively. The RGD residues are shown in green, and nitrogen,
oxygen atoms in blue and red, respectively. Ca(II) is represented
by a red sphere. Integrin and ligand residues involved in binding
are labeled with the three- and one-letter code, respectively.
Dotted lines denote H-bonds between ligands and integrin
(Reproduced with permission from J. Cell Sci., 2011, 124, 515, 2011
The Company of Biologists Ltd) Supplementary information for
Synthetic Receptors for Biomolecules: Design Principles and
Applications The Royal Society of Chemistry 2015
Slide 4
Figure 8.3 Complex structures showing: (top) vancomycin and
mimic of the normal bacteria cell wall peptidyl fragment
Ac2-L-Lys-D-Ala-D-Ala, (bottom) modified vancomycin analog and
mimic of the drug resistant bacteria cell wall peptidyl fragment
Ac2-L-Lys-D-Ala-D-Lac. Supplementary information for Synthetic
Receptors for Biomolecules: Design Principles and Applications The
Royal Society of Chemistry 2015
Slide 5
Figure 8.4 Receptors based on guanidinium groups. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 6
Figure 8.5 Receptors based on imidazolium groups. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 7
Figure 8.6 Receptor based on a viologen group. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 8
Figure 8.7 Receptor mainly based on hydrogen bonding.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 9
Figure 8.8 Copper containing receptors for amino acid
recognition based on indicator-displacement assays. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 10
Figure 8.9 Rhodium containing receptor for amino acid
recognition based on indicator-displacement assays. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 11
Figure 8.10 Au + containing receptor for amino acid
recognition. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 12
Figure 8.11 Schematic representation of the amino acid (Lys,
Arg or His) induced aggregation of calix-capped gold nanoparticles.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 13
Figure 8.12 Reaction of coumarin receptors with unprotected
amino acids. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 14
Figure 8.13 Recognition of Lysine by imine bond formation.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 15
Figure 8.14 Reaction based recognition of amino acids (Cys and
Hcy). Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 16
Figure 8.15 Reaction of 8.27 with sulfur-containing amino acids
(Cys, Hcy, and GSH). Supplementary information for Synthetic
Receptors for Biomolecules: Design Principles and Applications The
Royal Society of Chemistry 2015
Slide 17
Figure 8.16 Reaction based recognition of cysteine with 8.28.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 18
Figure 8.17 Reaction of 8.29 with thiol-containing amino acids.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 19
Figure 8.18 Cyclodextrin-nickel salophen complexes for
recognition of L-Phe-D-Pro containing peptides in water.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 20
Figure 8.19 Cyclodextrin based receptors for peptides.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 21
Figure 8.20 Bis-cyclodextrin receptors used for binding
dipeptides. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 22
Figure 8.21 C ucurbit[n]uril (Qn) host. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 23
Figure 8.22 Macrocyclic hosts 8.42 and 8.43 which
preferentially bind hydrophobic peptides in water. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 24
Figure 8.23 Self-assembled coordination cage 8.44 for peptide
binding in water. Supplementary information for Synthetic Receptors
for Biomolecules: Design Principles and Applications The Royal
Society of Chemistry 2015
Slide 25
Figure 8.24 Diketopiperazine based receptors. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 26
Figure 8.25 Cationic guanidinium based receptors. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015
Slide 27
Figure 8.26 General structure of 2-(guanidiniocarbonyl)pyrrole
functionalized receptor 8.49 and its interaction with a
tetrapeptide. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 28
Figure 8.27 2-(Guanidiniocarbonyl)pyrrole modified receptor
8.50. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 29
Figure 8.28 Ditopic receptors for RGD tripeptides.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 30
Figure 8.29 Crown ether containing peptide receptors.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 31
Figure 8.30 Crown ether containing peptide receptors.
Supplementary information for Synthetic Receptors for Biomolecules:
Design Principles and Applications The Royal Society of Chemistry
2015
Slide 32
Figure 8.31 Zn complexes for recognition of phosphorylated
peptide. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 33
Figure 8.32 Zn complexes for recognition of phosphorylated
peptides. Supplementary information for Synthetic Receptors for
Biomolecules: Design Principles and Applications The Royal Society
of Chemistry 2015
Slide 34
Figure 8.33 Peptide receptors based on the combination of crown
ether and metal complexes. Supplementary information for Synthetic
Receptors for Biomolecules: Design Principles and Applications The
Royal Society of Chemistry 2015
Slide 35
Figure 8.34 Histidine-coordinating Zn-nitrilotriacetic acid
complex receptors. Supplementary information for Synthetic
Receptors for Biomolecules: Design Principles and Applications The
Royal Society of Chemistry 2015
Slide 36
Figure 8.35 Histidine-coordinating Cu-nitrilotriacetic acid
complex receptors. Supplementary information for Synthetic
Receptors for Biomolecules: Design Principles and Applications The
Royal Society of Chemistry 2015
Slide 37
Figure 8.36 Metal complex receptors for peptides. Supplementary
information for Synthetic Receptors for Biomolecules: Design
Principles and Applications The Royal Society of Chemistry
2015