Synthesis of cyclic (alpha(2)beta)-tripeptides as potential peptide turn mimetics

Org Lett. 2002 Jun 27;4(13):2173-6. doi: 10.1021/ol025988b.

Abstract

[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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Models, Molecular
  • Molecular Mimicry
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Protein Structure, Secondary
  • Structure-Activity Relationship

Substances

  • Oligopeptides
  • Peptides, Cyclic