Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothioates)
- 1 January 1991
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 19 (21) , 5883-5888
- https://doi.org/10.1093/nar/19.21.5883
Abstract
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 (greater than 99%), this novel method allows preparation of oligo(nucleoside phosphorothioates) with predetermined chirality at each P-chiral internucleotide phosphorothioate centre.Keywords
This publication has 10 references indexed in Scilit:
- Regulation of Gene Expression with Double-Stranded Phosphorothioate OligonucleotidesScience, 1990
- Regulation of viral expression of human immunodeficiency virus in vitro by an antisense phosphorothioate oligodeoxynucleotide against rev (art/trs) in chronically infected cells.Proceedings of the National Academy of Sciences, 1989
- Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethorycarbunyl (Fmoc) for 5′-hydroryl protectionNucleic Acids Research, 1989
- Oligodeoxynucleoside phosphoramidates and phosphorothioates as inhibitors of human immunodeficiency virus.Proceedings of the National Academy of Sciences, 1988
- Phosphorothioate analogs of oligodeoxynucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus.Proceedings of the National Academy of Sciences, 1987
- An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistryNucleic Acids Research, 1987
- Synthesis and configurational analysis of a dinucleoside phosphate isotopically chiral at phosphorus. Stereochemical course of Penicillium citrinum nuclease P1 reactionBiochemistry, 1983
- Stereochemical course of the reaction catalyzed by 5'-nucleotide phosphodiesterase from snake venomBiochemistry, 1979
- Absolute configuration of the diastereomers of adenosine 5'-O-(1-thiotriphosphate): consequences for the stereochemistry of polymerization by DNA-dependent RNA polymerase from Escherichia coli.Proceedings of the National Academy of Sciences, 1978
- Stereospecific synthesis of thymidine cyclic 3',5' (SP)- and (RP)-phosphorothioatesJournal of the American Chemical Society, 1977