E. Ferrer et al., SYNTHESIS OF OLIGODEOXYNUCLEOTIDES CONTAINING 5-AMINOURACIL AND ITS N-ACETYL DERIVATIVE, Journal of the Chemical Society. Perkin transactions. I, (14), 1997, pp. 2051-2057
The preparation of oligonucleotides containing 5-amino-2'-deoxyuridine
is described, Three different protective groups for the amino functio
n of 5-aminouracil including trifluoroacetyl, dimethylformamidine and
2-(4-nitrophenyl)ethoxycarbonyl are analysed in order to reduce the ac
etylation of this base observed during the assembly of oligonucleotide
s 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.