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Mechanistic studies of oligo nucleotide chemical synthesis 12. role of pyridine in the phospho tri ester method of oligo nucleotide chemical synthesis



Mechanistic studies of oligo nucleotide chemical synthesis 12. role of pyridine in the phospho tri ester method of oligo nucleotide chemical synthesis



Bioorganicheskaya Khimiya 7(6): 900-906



The role of pyridine was studied in the internucleotide bond formation by the phosphotriester method of oligonucleotide chemical synthesis in the presence of p-toluenesulfonyl tetrazolide (TSTetr) and triisopropylbenzenesulfonyl chloride. Pyridine is a nucleophilic catalyst of the reaction of (ClC6H4)pT(Ac) with TSTetr leading to pyrophosphate tetraester (II) formation. The reaction of (II) with nucleoside (Tr)T [Tr = trityl] also requires nucleophilic catalyst. Pyridine or its derivatives play the role of nucleophilic catalyst in the absence of tetrazole. Tetrazole is the nucleophilic catalyst for the interaction of (II) with the nucleoside when arylsulfonyl tetrazolides are used, and pyridine plays the role of a general base catalyst accepting the proton from tetrazole. Diphenylphosphoryltetrazole, the analog of the proposed intermediate in the tetrazole-catalyzed pyrophosphate (II) reaction with nucleoside, reacts with (Tr)T in the absence of pyridine, however, pyridine accelerates this process, probably by the mechanism of base catalysis.

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