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The modes of binding methyl-alpha (and beta)-D-glucopyranosides and some of their derivatives to concanavalin A--a theoretical approach

Sekharudu, YC and Rao, VS (1984) The modes of binding methyl-alpha (and beta)-D-glucopyranosides and some of their derivatives to concanavalin A--a theoretical approach. In: Journal of Biomolecular Structure and Dynamics, 2 (1). pp. 41-54.

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Official URL: http://www.ncbi.nlm.nih.gov/pubmed/6400934

Abstract

The probable modes of binding of Methyl--alpha (and beta)-D-glucopyranosides and some of their derivatives to concanavalin A have been proposed from theoretical studies. Theory predicts that beta-MeGlcP can bind to ConA in three different modes whereas alpha-MeGlcP can bind only in one mode. beta-MeGlcP in its most favourable mode of binding differs from alpha-MeGlcP in its alignment in the active-site of the lectin where it binds in a flipped or inverted orientation. Methyl substitution at the C-2 atom of the alpha-MeGlcP does not significantly affect the possible orientations of the sugar in the active-site of the lectin. Methyl substitution at C-3 or C-4, however, affects the allowed orientations drastically leading to the poor inhibiting power of Methyl-3-O-methyl-alpha-D-glucopyranoside and the inactivity of Methyl-4-O-methyl-alpha-D-glycopyranoside. These studies suggest that the increased activity of the alpha-MeGlcP over beta-MeGlcP may be due to the possibility of formation of better hydrogen bonds and to hydrophobic interactions rather than to steric factors as suggested by earlier workers. These models explain the available NMR and other binding studies.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Adenine Presses
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 10 Feb 2010 05:11
Last Modified: 10 Feb 2010 05:11
URI: http://eprints.iisc.ernet.in/id/eprint/21988

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