Crystallographic characterization of the conformation of the 1-aminocyclohexane-1-carboxylic acid residue in simple derivatives and peptides

Valle, Giovanni and Crisma, Marco and Toniolo, Claudio and Sen, Nirupa and Sukumar, Muppalla and Balaram, Padmanabhan (1988) Crystallographic characterization of the conformation of the 1-aminocyclohexane-1-carboxylic acid residue in simple derivatives and peptides. In: Journal of the Chemical Society, Perkin Transactions 2 (3). pp. 393-398.

PDF 1988-01-01.pdf - Published Version Restricted to Registered users only Download (780kB) | Request a copy

Abstract

The crystal structures of 1-aminocyclohexane-1-carboxylic acid (H-Acc6-OH) and six derivatives (including dipeptides) have been determined. The derivatives are Boc-Acc6-OH, Boc-(Acc6)2-OH, Boc-L-Met-Acc6-OMe, ClCH2CO-Acc6-OH, p-BrC6H4CO-Acc6-OH oxazolone, and the symmetrical anhydride from Z-Acc6-OH, [(Z-Acc6)2O]. The cyclohexane rings in all the structures adopt an almost perfect chair conformation. The amino group occupies the axial position in six structures; the free amino acid is the only example where the carbonyl group occupies an axial position. The values determined for the torsion angles about the N–Cα(φ) and Cα–CO (ψ) bonds correspond to folded, potentially helical conformations for the Acc6 residue.

Item Type:	Journal Article
Publication:	Journal of the Chemical Society, Perkin Transactions 2
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited:	09 Nov 2010 10:14
Last Modified:	09 Nov 2010 10:14
URI:	http://eprints.iisc.ac.in/id/eprint/33534

Actions (login required)

View Item