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. 1983 Jun 11;11(11):3737–3751. doi: 10.1093/nar/11.11.3737

Synthesis and separation of diastereomers of deoxynucleoside 5'-O-(1-thio)triphosphates.

J T Chen, S J Benkovic
PMCID: PMC325999  PMID: 6856463

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.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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