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Deglycosylation of alkylated nucleosides: a molecular orbital study

Venkateswarlu, Divi and Lyngdoh, Duncan RH (1997) Deglycosylation of alkylated nucleosides: a molecular orbital study. In: Journal of Molecular Structure (Theochem), 418 (1). pp. 49-57.

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Abstract

The glycoside bond in alkylated nucleosides is known to be more stable for $0^6$ -alkylguanosines and $0^4$ - alkylthymines, and less stable for $N^3$ - and $N^7$ -alkylpurine and $O^2$ - alkylpyrimidine nucleosides. These marked differences have been demonstrated through in vitro acidic hydrolysis and in vivo glycosylase repair. This study examines the relative facility of the deglycosylation reaction for various nucleosides through the use of theoretical indices derived from the semiempirical AM1 SCF-MO methodology, which furnish inferences much in consonance with experiment.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Keywords: Alkylated nucleosides;Deglycosylation;Molecular orbital calculations;In vitro stability
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 23 Feb 2007
Last Modified: 19 Sep 2010 04:35
URI: http://eprints.iisc.ernet.in/id/eprint/9948

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