Title: Unexpected shift to a 4-imino tautomer upon N4-acylation of 5-methylcytosin-1-yl nucleoside analogues
Authors: Busson, Roger ×
Kerremans, Lucien
Van Aerschot, Arthur
Peeters, Oswald
Blaton, Norbert
Herdewijn, Piet #
Issue Date: 1999
Publisher: M. Dekker
Series Title: Nucleosides & Nucleotides vol:18 issue:4-5 pages:1079-1082
Abstract: In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analogues, 5-methylcytosine derivatives show upon N-4-benzoylation, commonly used as base protection in oligonucleotide synthesis, a tautomeric change of the base moiety from a 4-amino- into a 4-imino isomer. In the latter form, which is easily diagnosticized by C-13 NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.
ISSN: 0732-8311
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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