Unexpected shift to a 4-imino tautomer upon N-4-acylation of 5-methylcytosin-1-yl nucleoside analogues.

Citation
R. Busson et al., Unexpected shift to a 4-imino tautomer upon N-4-acylation of 5-methylcytosin-1-yl nucleoside analogues., NUCLEOS NUC, 18(4-5), 1999, pp. 1079-1082
Citations number
5
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES & NUCLEOTIDES
ISSN journal
0732-8311 → ACNP
Volume
18
Issue
4-5
Year of publication
1999
Pages
1079 - 1082
Database
ISI
SICI code
0732-8311(1999)18:4-5<1079:USTA4T>2.0.ZU;2-Z
Abstract
In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analo gues, 5-methylcytosine derivatives show upon N-4-benzoylation, commonly use d as base protection in oligonucleotide synthesis, a tautomeric change of t he base moiety from a 4-amino- into a 4-imino isomer. In the latter form, w hich is easily diagnosticized by C-13 NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.