Synthesis of Nucleoside 3′-Thiophosphates in One Step Procedure |
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Authors: | Maciej B Szczepanik Laurent Désaubry Roger A Johnson |
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Institution: | Department of Physiology and Biophysics, Health Sciences Center , State University of New York at Stony Brook , Stony Brook, NY, 11794, USA |
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Abstract: | Abstract A mild and efficient one-step method of thiophosphorylation was devised for acid-sensitive nucleosides. The procedure is based on thiophosphorylation of nucleoside magnesium alkoxide by 2-chloro-2-thio-1,3,2-dioxaphospholane. The utility and efficiency of this method combined with deprotection of the resulting cyclic triester were demonstrated by its application to the synthesis of both adenosine 3′- and 5′-thiophosphates. The procedure does not require protection of the exocyclic amino group and can be successfully used for the thiophosphorylation of nucleosides that are unusually sensitive to depurination. |
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