SYNTHESIS AND H-1 AND C-13 NMR SPECTRAL CHARACTERISTICS OF 8-BROMO-2',3'-DIDEOXYGUANOSINE AND 8-BROMO-2',3'-DIDEOXYINOSINE

Authors
ZEIDLER J GOLANKIEWICZ B
Citation
J. Zeidler et B. Golankiewicz, SYNTHESIS AND H-1 AND C-13 NMR SPECTRAL CHARACTERISTICS OF 8-BROMO-2',3'-DIDEOXYGUANOSINE AND 8-BROMO-2',3'-DIDEOXYINOSINE, Nucleosides & nucleotides, 15(5), 1996, pp. 1077-1095
Citations number
29
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
15
Issue
5
Year of publication
1996
Pages
1077 - 1095
Database
ISI
SICI code
0732-8311(1996)15:5<1077:SAHACN>2.0.ZU;2-R
Abstract
Reaction of 2',3'-dideoxyguanosine 1a as 5'-O-tert-butyldimethylsilyl derivative Ib and 2',3'-dideoxyinosine 2a with bromine in acetate buff er conducted in heterogeneous medium afforded 8-bromo-2',3'-dideoxygua nosine 3a (44% after deprotection) and 8-bromo-2',3'-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti --> syn on 8-bromo substitution of 2',3'-dideoxynucleosides is reflected in the H-1 and C-13 NMR spectra by characteristic shifts of H-2', H-3' , C-2' and C-3' signals.