Unexpected shift to a 4-imino tautomer upon N4-acylation of 5- methylcytosin-1-yl nucleoside analogues

Article abstract of DOI:10.1080/15257779908041652

In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analogues, 5-methylcytosine derivatives show upon N⁴-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 ¹³C NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.

Full text of DOI:10.1080/15257779908041652

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Unexpected Shift to a 4-Imino Tautomer
Upon N4-Acylation of 5-Methylcytosin-1-
yl Nucleoside Analogues
R. Busson a , L. Kerremans a , A. Van Aerschot a , M. Peeters b , N.
Blaton b & P. Herdewijn a
a Laboratory of Medicinal Chemistry, Rega Institute for Medical
Research , Minderbroedersstraat 10
b Laboratory for Analytical Chemistry and Medicinal
Physicochemistry , K. U. Leuven, Faculty of Pharmaceutical
Sciences , Van Evenstraat 4, B-3000, Leuven.
Published online: 04 Oct 2006.
To cite this article: R. Busson , L. Kerremans , A. Van Aerschot , M. Peeters , N. Blaton & P. Herdewijn
(1999) Unexpected Shift to a 4-Imino Tautomer Upon N4-Acylation of 5-Methylcytosin-1-yl Nucleoside
Analogues, Nucleosides and Nucleotides, 18:4-5, 1079-1082, DOI: 10.1080/15257779908041652
To link to this article: http://dx.doi.org/10.1080/15257779908041652
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