Tautomerism and Regioselectivity in Ribosylation of Guanine
- 1 May 1995
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 14 (3) , 287-290
- https://doi.org/10.1080/15257779508012363
Abstract
N2-acetyl- and 9, N2-diacetylguanines were subjected to reaction with tetraacetylribose in the presence of p-toluenesulfonic acid. Unlike the ribosylation of diacetylguanine, which gives 7-riboside as a kinetic product, the reaction of monoacetylguanine produces directly a mixture of 7- and 9-ribosides. This reflects N7H ⇆ N9H tautomerism of the guanine substrate and supports the hypothesis that only the unsubstituted nitrogens of the imidazolium portion of guanine (either N7 or N9) react directly with a sugar cation.Keywords
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