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The P‐Stereocontrolled Synthesis of PO/PS‐Chimeric Oligonucleotides by Incorporation of Dinucleoside Phosphorothioates Bearing an O ‐4‐Nitrophenyl Phosphorothioate Protecting Group
Author(s) -
Wozniak Lucyna A.,
Góra Marcin,
BukowieckaMatusiak Małgorzata,
Mourgues Sophie,
Pratviel Geneviève,
Meunier Bernard,
Stec Wojciech J.
Publication year - 2005
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.200400910
Subject(s) - chemistry , diastereomer , oligonucleotide , stereochemistry , aryl , stereospecificity , protecting group , chirality (physics) , exonuclease , chiral auxiliary , dna , biochemistry , organic chemistry , catalysis , enantioselective synthesis , alkyl , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , dna polymerase , quark
The synthesis of protected model dinucleoside (3',5')‐ O ‐aryl phosphorothioates, their separation into pure diastereomers, and their successful incorporation into oligonucleotides followed by stereospecific deprotection of the O ‐aryl phosphorothioate function with oximate ion (inversion) enables the preparation of chimeric PO/PS‐oligonucleotides with a predetermined sense of P ‐chirality at each internucleotide phosphorothioate position. The absolute configuration at the phosphorus of the internucleotide O ‐aryl phosphorothioate in “dimeric building blocks” has been assigned. The 3'‐terminal S P ‐phosphorothioate linkages effectively protect such chimeric constructs from degradation by human plasma exonuclease (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)