Reinvestigation into the Synthesis of Oligonucleotides Containing 5‐(β‐D‐Glucopyranosyloxymethyl)‐2′‐deoxyuridine.

Abstract

A reinvestigation into the synthesis of oligonucleotides containing 5-(β-D-glucopyranosyloxymethyl)-2′-deoxyuridine revealed that existing procedures for the preparation of these DNA fragments suffered from decomposition at the final deprotection step. The decomposition product was identified as the corresponding 5-(aminomethyl)-2′deoxyuridyl derivative arising from amino substitution of the β-D-glucosyl moiety during ammonolysis. This was shown to be suppressed by the use of phosphoramidite 21 in place of 12 for solid-phase oligonucleotide synthesis, in conjunction with short ammonia treatment at room temperature. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)