Glycosidic bond hydrolysis in septanosides: a comparison of mono-, di-, and 2-chloro-2-deoxy-septanosides

Dey, Supriya and Jayaraman, N (2014) Glycosidic bond hydrolysis in septanosides: a comparison of mono-, di-, and 2-chloro-2-deoxy-septanosides. In: CARBOHYDRATE RESEARCH, 399 . pp. 49-56.

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Abstract

A kinetic study of the hydrolytic stabilities of mono-, di-, and 2-chloro-2-deoxy septanosides, under acid-catalysis, is reported herein. A comparison of mono-and diseptanosides, shows that the glycosidic bond in the disaccharide is more stable than the monosaccharide. Further the glycosidic bond at the reducing end hydrolyzes almost twice as faster than that of the non-reducing end of the disaccharide. 2-Chloro-2-deoxy septanoside is found to be the most stable and its glycosidic bond hydrolysis occurs at elevated temperatures only. The orientation of the exo-cyclic hydroxymethyl group and the inductive effect are suggested to play a role in the rates of hydrolysis. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	CARBOHYDRATE RESEARCH
Publisher:	ELSEVIER SCI LTD
Additional Information:	Copyright for this article belongs to the ELSEVIER SCI LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLAND
Keywords:	Carbohydrates; Glycosidic bond; Hydrolysis; Kinetics; Septanosides
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	26 Dec 2014 06:49
Last Modified:	26 Dec 2014 06:49
URI:	http://eprints.iisc.ac.in/id/eprint/50517

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