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.

PDF P19830000417.pdf - Published Version Restricted to Registered users only Download (473kB) | Request a copy

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
Publication:	Perkin Transactions 1
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:	08 Feb 2010 08:17
Last Modified:	19 Sep 2010 05:39
URI:	http://eprints.iisc.ac.in/id/eprint/21874

Actions (login required)

View Item