Structural versatility of peptides containing C alpha, alpha-dialkylated glycines: conformational energy computations, i.r. absorption and 1H n.m.r. analysis of 1-aminocyclopropane-1-carboxylic acid homopeptides

Int J Biol Macromol. 1989 Dec;11(6):345-52. doi: 10.1016/0141-8130(89)90006-8.

Abstract

Conformational energy computations on the 1-aminocyclopropane-1-carboxylic acid mono-, di-, and tripeptide amides, Ac-(Ac3c)n-NHMe (n = 1-3), indicate that this C alpha, alpha-dialkylated, cyclic alpha-amino acid residue is conformally restricted and that type-I(I') beta-bends and distorted 3(10)-helices are particularly stable conformations for the di- and tripeptide amides, respectively. The results of the theoretical analysis are in agreement with those obtained in an i.r. absorption and 1H n.m.r. investigation in chloroform solution of Ac3c-rich tri- and tetrapeptide esters. A comparison is also made with the conclusions extracted from our previous work on peptides rich in Aib (alpha-aminoisobutyric acid), Ac5c (1-aminocyclopentane-1-carboxylic acid), and Ac6c (1-aminocyclohexane-1-carboxylic acid).

MeSH terms

  • Alkylation
  • Amino Acids / chemistry*
  • Amino Acids, Cyclic*
  • Glycine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Oligopeptides / chemistry*
  • Protein Conformation
  • Spectrophotometry, Infrared

Substances

  • Amino Acids
  • Amino Acids, Cyclic
  • Oligopeptides
  • 1-aminocyclopropane-1-carboxylic acid
  • Glycine