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Crystal structure of a tripeptide containing aminocyclododecane carboxylic acid: a supramolecular twisted parallel -sheet in crystals

Vasudev, Prema G and Aravinda, Subrayashastri and Shamala, Narayanaswamy (2016) Crystal structure of a tripeptide containing aminocyclododecane carboxylic acid: a supramolecular twisted parallel -sheet in crystals. In: JOURNAL OF PEPTIDE SCIENCE, 22 (3). pp. 166-173.

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Official URL: http://dx.doi.org/10.1002/psc.2854

Abstract

The crystal structure of a tripeptide Boc-Leu-Val-Ac(12)c-OMe (1) is determined, which incorporates a bulky 1-aminocyclododecane-1-carboxylic acid (Ac(12)c) side chain. The peptide adopts a semi-extended backbone conformation for Leu and Val residues, while the backbone torsion angles of the C-,C--dialkylated residue Ac(12)c are in the helical region of the Ramachandran map. The molecular packing of 1 revealed a unique supramolecular twisted parallel -sheet coiling into a helical architecture in crystals, with the bulky hydrophobic Ac(12)c side chains projecting outward the helical column. This arrangement resembles the packing of peptide helices in crystal structures. Although short oligopeptides often assemble as parallel or anti-parallel -sheet in crystals, twisted or helical -sheet formation has been observed in a few examples of dipeptide crystal structures. Peptide 1 presents the first example of a tripeptide showing twisted -sheet assembly in crystals. Copyright (c) 2016 European Peptide Society and John Wiley & Sons, Ltd.

Item Type: Journal Article
Publication: JOURNAL OF PEPTIDE SCIENCE
Publisher: WILEY-BLACKWELL
Additional Information: Copy right for this article belongs to the WILEY-BLACKWELL, 111 RIVER ST, HOBOKEN 07030-5774, NJ USA
Keywords: tripeptide; crystal structure; 1-aminocyclododecane-1-carboxylic acid; twisted -sheet
Department/Centre: Division of Physical & Mathematical Sciences > Physics
Date Deposited: 06 Apr 2016 04:59
Last Modified: 06 Apr 2016 04:59
URI: http://eprints.iisc.ac.in/id/eprint/53455

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