Structural Biochemistry. 20. Methylation of Purine Nucleosides

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

doi:10.1021/jo01309a002

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 language	English (US)
Pages (from-to)	4073-4076
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	45
Issue number	21
DOIs	https://doi.org/10.1021/jo01309a002
State	Published - Oct 1980

ASJC Scopus subject areas

Organic Chemistry

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title = "Structural Biochemistry. 20. Methylation of Purine Nucleosides",

abstract = "Experimental methods have been devised for the permethylation of both adenosine (la{\textregistered} lb) and guanosine (2a{\textregistered}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{\textregistered}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.",

author = "Pettit, {George R.} and Blazer, {Richard M.} and Einck, {James J.} and George Pettit",

year = "1980",

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language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - Structural Biochemistry. 20. Methylation of Purine Nucleosides

AU - Pettit, George R.

AU - Blazer, Richard M.

AU - Einck, James J.

AU - Pettit, George

PY - 1980/10

Y1 - 1980/10

N2 - 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.

AB - 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.

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Structural Biochemistry. 20. Methylation of Purine Nucleosides

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