Synthesis and Photoreaction of 4"-Pivaloyl Guanosides

Abstract

The synthesis of a 4’-pivaloylated guanosine and its incorporation into oligonucleotides is described. Photolysis of the modified nucleoside and DNA double strand leads in nearly quantitative yield to enol ethers. The decisive step in this reaction is a very fast electron transfer from guanine to an enol ether radical cation.

Key words

nucleosides - oligonucleotides - radicals - electron transfer - photochemistry

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