Design, synthesis, and application of azabicyclo[X.Y.0]alkanone amino acids as constrained dipeptide surrogates and peptide mimics.
Azabicyclo[X.Y.0]alkanone amino acids are challenging synthetic targets and useful tools for studying structure-activity relationships of native peptide ligands. They have been employed to increase potency and stability in conformationally rigid enzyme inhibitors and receptor ligands. Since last reviewed in 1997, activity in their synthesis and application has increased significantly and access is now available to a wider diversity of these peptide mimics. This review focuses on recent syntheses of these heterocyclic amino acids and their application in the investigation of biologically active peptides and peptide mimics.
Cluzeau
Jérôme
J
Département de Chimie, Université de Montréal, Montréal H3C 3J7, Québec, Canada.
Lubell
William D
WD
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D018716:Molecular Mimicry; D015394:Molecular Structure
D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004151:Dipeptides