Synthesis and separation of diastereomers of deoxynucleoside 5’– 0(l–thio)triptaosphates
- 1 January 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 11 (11) , 3737-3751
- https://doi.org/10.1093/nar/11.11.3737
Abstract
Treatment of unprotected nucleosides with an excess of phosphorous acid and stoichiometric proportions of N,N'-di-p-tolylcarbodiimide in anhydrous pyridine gives predominantly deoxynucleoside monophosphites and minor amounts of 5' :3'-diphosphites; for deoxyadenosine and deoxyguanosine, the monophosphite products are exclusively 5'-phosphites, whereas for deoxycytidine and thymidine, the yields of the 5'-phosphites are 85% and 92% respectively. Sulfurization of these deoxynucleoside monophosphites with sulfur in the presence of trialkylamines and trimethylsilyl chloride in dry pyridine nearly quantitatively produces deoxynucleoside phosphorothioates. Condensation of these phosphorothioates with pyrophosphate forms diastereomers of the alpha-thio-derivatives of deoxynucleoside triphosphate. The individual diastereomers of each deoxynucleoside 5'-O-(1-thio)triphosphate can be separated, on a preparative scale, by ion exchange chromatography.Keywords
This publication has 17 references indexed in Scilit:
- Gap misrepair mutagenesis: efficient site-directed induction of transition, transversion, and frameshift mutations in vitro.Proceedings of the National Academy of Sciences, 1982
- [14] Stereochemistry of selected phosphotransferases and nucleotidyltransferasesPublished by Elsevier ,1982
- Crystal and Molecular Structure of Adenosine 5'-O-Phosphorothioate O-p-Nitrophenyl Ester (Sp Diastereomer). Substrate Stereospecificity of Snake Venom PhosphodiesteraseEuropean Journal of Biochemistry, 1979
- Stereochemical course of the reaction catalyzed by 5'-nucleotide phosphodiesterase from snake venomBiochemistry, 1979
- 31P nuclear magnetic resonance spectra of the thiophosphate analogs of adenine nucleotides; effects of pH and Mg2+ bindingBiochemistry, 1978
- Novel phosphonothioate substrates for phosphodiesterasesJournal of the American Chemical Society, 1977
- Synthesis and properties of diastereoisomers of adenosine 5'-(O-1-thiotriphosphate) and adenosine 5'-(O-2-thiotriphosphate)Biochemistry, 1976
- Silyl phosphites. I. Reaction of silyl phosphites with diphenyl disulfide. Synthesis of S-phenyl nucleoside phosphorothioatesJournal of the American Chemical Society, 1974
- On the Mechanism of Ribonuclease AEuropean Journal of Biochemistry, 1974
- Nucleoside phosphorothioatesJournal of the American Chemical Society, 1970