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CHEMICAL REACTIONS IN DOUBLE-STRANDED NUCLEIC ACIDS. IX. DIRECTED INTRODUCTION OF SUBSTITUTED PYROPHOSPHATE BONDS INTO DNA STRUCTURE
S. A. KUSNETSOVA, M. G. IVANOVSKAYA, Z. A. SHABAROVA
Department of Chemistry, M. V. Lomonosov Moscow State University
Abstract: An effective synthesis of oligodeoxyribonucleotides containing a substituted pyrophosphate bond in the definite position of the sugar-phosphate backbone has been developed by template-directed condensation of two heptanucleotides. One of them containing 5'-phosphate group to be activated and 3'-phosphate group of the other being substituted with ethoxy-, buthylamino-, morpholino- or ethyl glycinate residues. Waler-soluble carbodiimide (EDAC) proved to be more efficient in the phosphate group activation than N-hydroxybenzotriazole ester; (yields of substituted pyrophosphates 35–80 and 10–15% respectively). The substituted pyrophosphate bond is quite stable in neutral aqueous solution. Mild conditions of selective cleavage of this bond yielding the initial oligonucleotides were found.
Russian Journal of Bioorganic Chemistry 1990, 16 (2):219-225