Stereochemistry of peptides containing 1-aminocyclopentane carboxylic acid (Acc5). Solution and solid state conformations of Boc-Acc5-Acc5-NHMe.

Bardi, R and Piazzesi, AM and Toniolo, C and Balaram, Padmanabhan and Sukumar, M (1986) Stereochemistry of peptides containing 1-aminocyclopentane carboxylic acid (Acc5). Solution and solid state conformations of Boc-Acc5-Acc5-NHMe. In: Biopolymers, 25 (9). pp. 1635-1644.

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Abstract

The conformational analysis of a protected homodipeptide of 1-aminocyclopentanecarboxylic acid (Acc5) has been carried out. 1H-nmr studies establish a ?-turn conformation for Boc-Acc5-Acc5-NHMe in chloroform and dimethylsulfoxide solutions involving the methylamide NH in an intramolecular hydrogen bond. Supportive evidence for the formation of an intramolecular hydrogen bond is obtained from ir studies. X-ray diffraction studies reveal a type III ?-turn conformation in the solid state stabilized by a 4 ? 1 hydrogen bond between the Boc CO and methylamide NH groups. The ?,? values for both Acc5 residues are close to those expected for an ideal 310-helical conformation (?? ± 60°, ?? ±30°).

Item Type:	Journal Article
Publication:	Biopolymers
Publisher:	John Wiley & Sons
Additional Information:	copyright of this article belongs to John Wiley & Sons.
Department/Centre:	Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited:	29 Oct 2010 07:39
Last Modified:	29 Oct 2010 07:39
URI:	http://eprints.iisc.ac.in/id/eprint/33519

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