NOVEL ROUTE TO OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES) - STEREOCONTROLLED SYNTHESIS OF P-CHIRAL OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES)

被引:147
作者
STEC, WJ
GRAJKOWSKI, A
KOZIOLKIEWICZ, M
UZNANSKI, B
机构
[1] Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Department of Bioorganic Chemistry, Lodz 90-363
关键词
D O I
10.1093/nar/19.21.5883
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis and separation of diastereoisomerically pure 5'-O-DMT-nucleoside 3'-O-(2-thio-1,3,2-oxathiaphospholane) allows their use as synthons in DBU-catalyzed reaction with the 5'-hydroxyl function of solid-support-bound nucleoside moiety. Since this reaction is stereospecific (> 99%), this novel method allows preparation of oligo(nucleoside phosphorothioates) (1) with predetermined chirality at each P-chiral internucleotide phosphorothioate centre.
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页码:5883 / 5888
页数:6
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