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

Abstract

AbstractA 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)