Journal
TETRAHEDRON LETTERS
Volume 48, Issue 31, Pages 5475-5479Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.05.170
Keywords
phosphorothioates; nucleotide analogues; phosphorimidazolides; chemical synthesis
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A straightforward method for the synthesis of nucleotide analogues bearing a phosphorothioate moiety at the terminal position of the polyphosphate chain is described. Several nucleoside 5'-(2-thiodiphosphates) and 5'-(3-thiotriphosphates) were synthesized by treatment of the appropriate nucleotide imidazolide derivative with a ca. 4-fold excess of thiophosphate triethylammonium salt in DMF in the presence of zinc chloride. The HPLC reaction yields varied from 80% to 100%, in the majority of cases exceeding 90%. Separation was accomplished by Sephadex ion-exchange chromatography or reverse-phase HPLC with preparative yields of about 70%. (c) 2007 Elsevier Ltd. All rights reserved.
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