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Increased glycosidic bond stabilities in 4-C-hydroxymethyl linked disaccharides

Daskhan, Gour Chand and Jayaraman, Narayanaswamy (2011) Increased glycosidic bond stabilities in 4-C-hydroxymethyl linked disaccharides. In: Carbohydrate Research, 346 (15). pp. 2394-2400.

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Official URL: http://dx.doi.org/10.1016/j.carres.2011.08.030


Three new hydroxymethyl-linked non-natural disaccharide analogues, containing an additional methylene group in between the glycosidic linkage, were synthesized by utilizing 4-C-hydroxymethyl-alpha-D-glucopyranoside as the glycosyl donor. A kinetic study was undertaken to assess the hydrolytic stabilities of these new disaccharide analogues toward acid-catalyzed hydrolysis, at 60 degrees C and 70 degrees C. The studies showed that the disaccharide analogues were stable, by an order of magnitude, than naturally-occurring disaccharides, such as, cellobiose, lactose, and maltose. The first order rate constants were lower than that of methyl glycosides and the trend of hydrolysis rate constants followed that of naturally-occurring disaccharides. alpha-Anomer showed faster hydrolysis than the beta-anomer and the presence of axial hydroxyl group also led to faster hydrolysis among the disaccharide analogues. Energy minimized structures, derived through molecular modeling, showed that dihedral angles around the glycosidic bond in disaccharide analogues were nearly similar to that of naturally-occurring disaccharides. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Carbohydrate Research
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Acid hydrolysis;Carbohydrates;Disaccharide analogues; Glycosidic bond;Kinetics;Oxocarbenium ion
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 21 Dec 2011 09:22
Last Modified: 21 Dec 2011 09:34
URI: http://eprints.iisc.ac.in/id/eprint/42609

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