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The Interaction of Trihalogenoacetic Anhydrides and Trihalogenoacetyl Chlorides with Thymidine 5′-Phosphate as an Approach to New Activating Agents in the Phosphorylation Reactions for Nucleotides
Bogachev,Ulanov
, p. 56 - 65 (2007/10/03)
The interaction of thymidine 5′-phosphate with trichloroacetic anhydride, trichloroacetyl chloride, and tribromoacetyl bromide was studied in dimethylformamide and acetonitrile in the presence of tertiary amines. The first two reactions gave the mixed anhydride of trichloroacetic and thymidylic acids (acyl phosphate) as the major product and P1,P 2-dithymidine 5′-pyrophosphate as the byproduct. The third reaction proceeded by a more complicated mechanism and mainly led to substituted polyphosphates. The subsequent treatment of the reaction mixtures with morpholine resulted in thymidine 5′-phosphoromorpholidate in a high yield. The phosphorylating activities of the trichloroacetyl and tribromoacetyl phosphates were 77 and 89%, respectively.
