Synthesis of cyclic (alpha(2)beta)-tripeptides as potential peptide turn mimetics.
[reaction: see text] The solid-supported synthesis followed by cyclization in solution of cyclic (alpha(2)beta)-tripeptides, potential peptide beta-turn mimetics, is described. The cyclization takes advantage of facilitating the rotation between trans- and cis-rotamers of two amide bonds. The method is amenable to combinatorial approaches as is illustrated by the synthesis of a small array of cyclic (alpha(2)beta)-tripeptides.
Wels
Bas
B
Department of Medicinal Chemistry, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands.
Kruijtzer
John A W
JA
Liskamp
Rob M J
RM
D008958:Models, Molecular; D018716:Molecular Mimicry; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D013329:Structure-Activity Relationship
D009842:Oligopeptides; D010456:Peptides, Cyclic