Tautomerism and regioselectivity in ribosylation of guanine

Article abstract of DOI:10.1080/15257779508012363

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 right arrow-left arrow 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.

Full text of DOI:10.1080/15257779508012363

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Nucleosides and Nucleotides
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Tautomerism and Regioselectivity in
Ribosylation of Guanine
Jerzy Boryski a & Andrzej Manikowski a
a Institute of Bioorganic Chemistry, Polish Academy of Sciences ul ,
Noskowskiego, 12/14, PL-61704, Pozna′, Poland
Published online: 16 Feb 2007.
To cite this article: Jerzy Boryski & Andrzej Manikowski (1995) Tautomerism and Regioselectivity in
Ribosylation of Guanine, Nucleosides and Nucleotides, 14:3-5, 287-290
To link to this article: http://dx.doi.org/10.1080/15257779508012363
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