Synthesis and binding properties of a macrobicyclic receptor for N-protected peptides with a carboxylic acid terminus

Beta-Strand Mimetics

“…Additional amide functionality around the rim of the bowl-shaped structure provides hydrogen-bonding sources to interact with peptide guest molecules. NMR spectroscopic studies concluded that macrocycle 17 was a flexible receptor, able to bind Cbz-β-alanyl- d -alanine substrate within the macrocyclic cavity via a series of well-defined hydrogen bonds making the peptidic substrate an extended conformation . In addition, an acyclic variant of 17 was reported by the same group …”

“…Synthetic macrocyclic receptors incorporating a carboxylic acid binding site specifically for peptides with a free carboxylic acid terminus have been developed . One such macrocyclic structure, 17 , has a diamidopyridine unit at the base of an open, bowl-shaped cavity.…”

Development of a Synthetic Receptor for the Food Toxin Beauvericin: A Tale of Carbazole and Steroids

“…A wealth of artificial receptors has been developed for a broad range of ligands such as anions, cations, saccharides and small linear dipeptides and tripeptides, to name just a few. In the context of peptide ligand binding, association constants in the range of 10 3 –10 6 M –1 have been reported. − However, cyclic medium-sized depsipeptides such as beauvericin have remained unexplored as ligands for synthetic hosts. In terms of ligand scope, the work presented herein is a first step toward filling this gap.…”

Synthesis and C2‐symmetric structure of a cyclotetrapeptide composed of anthranilic acid and leucine

“…1), molecular clefts such as Tröger's base,1 Kagan's ether,2 and the related dibenzobicyclo[3.3.1]nonane3 are very attractive chiral C 2 ‐symmetrical molecules ( 2 ). In the field of host–guest chemistry, relatively large bowls ( 3 )4–7 and cavities8 have been constructed by chiral C 2 ‐symmetric cyclic tetrapeptides. Although cyclic tetrapeptides having a chiral C 2 ‐symmetric structure might be candidates for a chiral C 2 ‐bowl‐shaped structure, there are very few examples of apparent bowl‐shaped cyclic tetrapeptides such as cyclo‐β‐tetrapeptides,9, 10 tetrapeptides composed of alternating proline and 3‐aminobenzoic acid,11 and cyclic tetrapeptides with alternating β‐furanoid sugar amino acid and ornithine 12.…”