ENZYMATIC ALCOHOLYSIS OF SO2-URACIL ANALOG DIACYCLONUCLEOSIDES - LONG-DISTANCE EFFECT OF THE SUBSTITUENTS ON THE REGIOSELECTIVITY

Authors
CONDE S ESTEBAN AI ALONSO D LOPEZSERRANO P MARTINEZ A
Citation
S. Conde et al., ENZYMATIC ALCOHOLYSIS OF SO2-URACIL ANALOG DIACYCLONUCLEOSIDES - LONG-DISTANCE EFFECT OF THE SUBSTITUENTS ON THE REGIOSELECTIVITY, Journal of molecular catalysis. B, Enzymatic, 4(5-6), 1998, pp. 295-302
Citations number
12
Categorie Soggetti
Chemistry Physical
Journal title
Journal of molecular catalysis. B, Enzymatic → ACNP
ISSN journal
13811177
Volume
4
Issue
5-6
Year of publication
1998
Pages
295 - 302
Database
ISI
SICI code
1381-1177(1998)4:5-6<295:EAOSAD>2.0.ZU;2-6
Abstract
Diacetoxy SO2-uracil analog diacyclonucleosides have been deprotected via Lipase-mediated alcoholysis. The reactivity and regioselectivity o f the reaction are dependent on the steric hindrance of distant 5-subs tituents, even if they are as small as a methyl or a 4,5-trimethylene chain, and, in a lesser extent, the electronic or hydrogen bond intera ctions of 3-carbonyl and hydroxyl-chain groups. (C) 1998 Elsevier Scie nce B.V. All rights reserved.