Structural analysis of β-turn mimics containing a substituted 6-aminocaproic acid linker

O. Kitagawa, Osamu Kitagawa, D. Dutta, M. Morton, F. Takusagawa, J. Aube

Research output: Contribution to journalArticle

41 Citations (Scopus)

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
Externally publishedYes

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Aminocaproic Acid
Structural analysis
Stereochemistry
Stereoisomerism
Acids
Dipeptides
X ray crystallography
Dichroism
Peptides
Nuclear magnetic resonance spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Structural analysis of β-turn mimics containing a substituted 6-aminocaproic acid linker. / Kitagawa, O.; Kitagawa, Osamu; Dutta, D.; Morton, M.; Takusagawa, F.; Aube, J.

In: Journal of the American Chemical Society, Vol. 117, No. 19, 1995, p. 5169-5178.

Research output: Contribution to journalArticle

Kitagawa, O. ; Kitagawa, Osamu ; Dutta, D. ; Morton, M. ; Takusagawa, F. ; Aube, J. / Structural analysis of β-turn mimics containing a substituted 6-aminocaproic acid linker. In: Journal of the American Chemical Society. 1995 ; Vol. 117, No. 19. pp. 5169-5178.
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