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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, Universittsstrasse 7, 45141 Essen, Germany *Email: carsten.schmuck@uni-due.de Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications The Royal Society of Chemistry 2015

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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Figure 8.24 Diketopiperazine based receptors. Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications The Royal Society of Chemistry 2015

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Figure 8.25 Cationic guanidinium based receptors. Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications The Royal Society of Chemistry 2015

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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