Trishomocubane amino acid as a beta-turn scaffold

Chem Biol Drug Des. 2008 Feb;71(2):125-30. doi: 10.1111/j.1747-0285.2007.00618.x. Epub 2008 Jan 17.

Abstract

The synthesis and X-ray structure of two diasteriomeric heptapeptides [Ac-Ala-Ala-Ala-(R/S)-Cage-Ala-Ala-Ala-NH2] with a trishomocubane amino acid as a beta-turn scaffold are reported. The amino acid was synthesized as a racemate and two diastereomeric peptides were obtained. The two peptides were separated by preparative high-pressure liquid chromatography and crystals suitable for X-ray analysis were grown for both diasteriomeric peptides. In general, both the peptides satisfy the criteria for beta-turn conformations. Five of the six Ala residues of both cage peptide crystals satisfy the criteria for 3(10)-helix characteristics and the cage amino acid residue satisfied the alpha-helix classification. These experimental results confirm previous theoretical studies in our laboratory which predicted that the cage moiety would be a strong/active beta-turn inducer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Molecular Mimicry
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Protein Structure, Secondary*
  • Stereoisomerism

Substances

  • Amino Acids
  • Oligopeptides