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Nucleic Acids Research, 1984, Vol. 12, No. 23 9123-9135
© 1984

CHEMISTRY

Synthesis and reactions of a nucleoside derivative of phosphoric sulfonic anhydride. Studies related to the mechanisms of coupling reactions in the chemical synthesis of oligodeoxyribonucleotides by phosphotriesier procedures

W. Dabkowslri, Z. Skrzypczynski, J. Micnalshi, N. Piel, L.W. McLaughlin and F. Cramer

Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences Boczna 5, 90-362 Lodz, Poland Max-Planck-Institut für experimentelle Medizin, Abteilung Chemie, Hermann-Rein-Strasse 3 D-3400 Gottingen, FRG

Received October 1, 1984. Revised November 9, 1984. Accepted November 9, 1984.

The synthesis of a model compound, diphenylphosphoric toluene-p-sulfonic anhydride, an arylsubstituted phosphoric sulfonic mixed anhydride, is described. Using the same procedure a thymidyl substituted derivative was prepared. The phosphoric sulfonic anhydride is the presumed intermediate in oligonucleo-tide coupling reactions involving phosphodiester activation by arenesulfonyl derivatives. This mixed anhydride reacts with a variety of nucleophiles. It can be converted to phophotriester derivatives in the presence of simple alcohols. Phosphotriester formation using the 5'-hydroxyl of a thymidine derivative requires additionally a catalyst such as N-methylimidazole. The reactive intermediate produced upon the addition of N-methylimidazole to.the phosphoric sulfonic anhydride has been observed spectroscoplcally using 31P-NMR.


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