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Conformationally stable and constrained macrocarbocyclic pseudopeptide mimics of beta-hairpin structures
Stephen Hanessian1, Mauro Angiolini
1Department of Chemistry, Université de Montréal, QC, Canada. stephen.hanessian@umontreal.ca
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 2, 2002
Abstract:
Subjecting a D-Pro-L-Pro template harboring N- and C-terminal omega-alkenyl amino acids to a ring-closure metathesis reaction afforded the corresponding macrocyclic alkenes. A cis-alkene analogue crystallized with one molecule each of water and chloroform, which were retained even after heating at 100 degrees C. By using the reduced macrocyclic product as a template, the metathesis could be repeated twice on newly installed omega-alkenyl amino acids to give three-tiered macrocarbocyclic pseudopeptides as mixtures of conformers. NMR studies revealed the high conformational stability of these motifs.