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Molecular structure of Boc-Aib-Aib-Phe-Met-NH2·DMSO. A fragment of a biologically active enkephalin analogue

Prasad, BVV and Sudha, TS and Balaram, V (1982) Molecular structure of Boc-Aib-Aib-Phe-Met-NH2·DMSO. A fragment of a biologically active enkephalin analogue. In: Perkin Transactions 1 (2). pp. 417-421.

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Abstract

The tetrapeptide t-butyloxycarbonyl--aminoisobutyryl--aminoisobutyryl-L- phenylalanyl-L-methionyl amide crystallizes in the orthorhombic space group P212121 with a= 9.096, b= 18.067, c= 21.701 Å and Z= 4. The crystals contain one molecule of dimethyl sulphoxide (DMSO) associated with each peptide. The structure has been solved by direct methods and refined to an R value of 0.103 for 2 672 observed reflections. The peptide adopts a distorted 310 helical structure stabilized by two intramolecular 4 1 hydrogen bonds between the Boc CO and Aib(1) CO groups and the NH groups of Phe(3) and Met(4), respectively. A long hydrogen bond (N O = 3.35 Å) is also observed between Aib(2) CO and one of the terminal amide hydrogens. The DMSO molecule is strongly hydrogen bonded to the Aib(1) NH group. The solid-state conformation agrees well with proposals made on the basis of n.m.r. studies in solution.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 08 Feb 2010 08:17
Last Modified: 19 Sep 2010 05:39
URI: http://eprints.iisc.ernet.in/id/eprint/21874

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