Stereoselective synthesis of individual isomers of Leu-enkephalin analogues containing substituted beta-turn bicyclic dipeptide mimetics

Chem Commun (Camb). 2003 Jul 7:(13):1598-9. doi: 10.1039/b302235h.

Abstract

Novel constrained beta-turn dipeptide mimetics, 8-phenyl thiaindolizidinone amino acids 3, have been synthesized stereoselectively and incorporated into Leu-enkephalin peptides as a replacement of dipeptide Gly3-Phe4 to afford four individual isomers of Leu-enkephalin analogues 6.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Substitution*
  • Dipeptides / chemical synthesis
  • Enkephalin, Leucine / analogs & derivatives*
  • Enkephalin, Leucine / chemical synthesis*
  • Molecular Mimicry*
  • Protein Structure, Secondary
  • Stereoisomerism

Substances

  • Dipeptides
  • Enkephalin, Leucine