Structural Analysis of β-Turn Mimics Containing a Substituted 6-Aminocaproic Acid Linker

Fusao Takusagawa, Osamu Kitagawa, David Vander Velde, Dinah Dutta, Martha Morton, Jeffrey Aubé

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Abstract

A series of β-turn models have been prepared consisting of the dipeptide Ala-Gly cyclized with all stereoisomers of 6-amino-3,5-dimethylcaproic acid and 6-amino-3-methylcaproic acid, as were related peptides based on Gly-Gly and Ala-Ala. The requisite linkers were made using routes featuring stereoselective ring-expansion reactions and the syntheses completed using standard methodology. A preliminary examination of these compounds has been carried out using NMR spectroscopy, circular dichroism, and, in several cases, X-ray crystallography. These studies indicate that, depending on linker stereochemistry, different proportions of type II and type I turns were observed in solution. Both type I and type II turns were observed in the solid state.

Original languageEnglish
Pages (from-to)5169-5178
Number of pages10
JournalJournal of the American Chemical Society
Volume117
Issue number19
DOIs
Publication statusPublished - 1995 May

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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