Structural Biochemistry. 20. Methylation of Purine Nucleosides

George R. Pettit, Richard M. Blazer, James J. Einck, George Pettit

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Abstract

Experimental methods have been devised for the permethylation of both adenosine (la® lb) and guanosine (2a®1- 2b + 3a) employing trimethylanilinium methoxide (TMAM). Reaction of the TMAM reagent with inosine (5a) and xanthosine (11) was found to promote imidazole ring and/or riboside cleavage (e.g., 5a®7a and 10). While methylation of inosine resulted in a variety of such reaction pathways, xanthosine followed essentially a single direction, leading to caffeine (12) as the major product. Reaction conditions developed for permethylation of these purine nucleosides with the TMAM reagent should prove useful with other such heterocyclic glycoside systems.

Original languageEnglish (US)
Pages (from-to)4073-4076
Number of pages4
JournalJournal of Organic Chemistry
Volume45
Issue number21
DOIs
StatePublished - Oct 1980

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ASJC Scopus subject areas

  • Organic Chemistry

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