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Reinvestigation into the Synthesis of Oligonucleotides Containing 5‐(β‐ D ‐Glucopyranosyloxymethyl)‐2′‐deoxyuridine
Author(s) -
Turner John J.,
Meeuwenoord Nico J.,
Rood Anita,
Borst Piet,
van der Marel Gijs A.,
van Boom Jacques H.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300218
Subject(s) - chemistry , oligonucleotide , phosphoramidite , moiety , oligonucleotide synthesis , stereochemistry , decomposition , derivative (finance) , combinatorial chemistry , deoxyuridine , organic chemistry , dna , biochemistry , economics , financial economics
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)