Chapter 8. Synthetic Receptors for Amino Acids and Peptides Debrabata Maity and Carsten Schmuck* University of Duisburg-Essen, Faculty of Chemistry, Universitätsstrasse 7, Essen, Germany * Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications © The Royal Society of Chemistry 2015

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

Figure 8.2 Model of the binding interaction between the RGD peptide (Arg-Gly-Asp) and binding site of α v β 3 - integrin. α- and β-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

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

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

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

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

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

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

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

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

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

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

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

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

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

Figure 8.16 Reaction based recognition of cysteine with Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications © The Royal Society of Chemistry 2015

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

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

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

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

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

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

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

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

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

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

Figure (Guanidiniocarbonyl)pyrrole modified receptor Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications © The Royal Society of Chemistry 2015

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

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

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

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

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

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

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

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

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