Peptide sweeteners. 3. Effect of modifying the peptide bond on the sweet taste of L-aspartyl-L-phenylalanine methyl ester and its analogues

J Med Chem. 1980 Apr;23(4):413-20. doi: 10.1021/jm00178a012.

Abstract

A series of analogues designed to assess the importance of the amide bond in the dipeptide sweetener L-aspartyl-L-phenylalanine methyl ester has been synthesized and tested. The peptide bond was methylated, replaced by an ester bond, or reversed. all of these modifications produced compounds that did not have a sweet taste. We conclude that the steric, electronic, and directional characteristics of the amide bond are essential for biological activity in the dipeptide sweeteners.

Publication types

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

MeSH terms

  • Aspartame / analogs & derivatives*
  • Aspartame / chemical synthesis
  • Aspartame / pharmacology
  • Dipeptides / analogs & derivatives*
  • Humans
  • Ions
  • Molecular Conformation
  • Structure-Activity Relationship
  • Sweetening Agents / chemical synthesis
  • Sweetening Agents / pharmacology*

Substances

  • Dipeptides
  • Ions
  • Sweetening Agents
  • Aspartame