Synthesis of oligodeoxynucleotides containing 5-aminouracil and its N-acetyl derivative

Abstract

The preparation of oligonucleotides containing 5-amino-2′-deoxyuridine is described. Three different protective groups for the amino function of 5-aminouracil including trifluoroacetyl, dimethylformamidine and 2-(4-nitrophenyl)ethoxycarbonyl are analysed in order to reduce the acetylation of this base observed during the assembly of oligonucleotides containing this base analogue. The side-reaction is avoided by using the base-labile 2-(4-nitrophenyl)ethoxy as protecting group and 2-(4-nitrophenyl)ethyl chloroformate during the capping step.

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