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Nucleic Acids Research, 1978, Vol. 5, No. 4 1253-1272
© 1978

Articles

The reactivity of phosphomono-and phosphodiester groups in oligonucleotides

D. G. Knorre, V. F. Zarytova, A. V. Lebedev, L. M. Khalimskaya and E. A. Sheshegova

Institute of Organic Chemistry, Siberian Division of the Academy of Sciences of USSR Novosibirsk, 630090, USSR

Received December 19, 1977. The rate constants were estimated by phosphorus NMR spectro-scopy for the reactions of alcohols (Tr-dT, 2-cyanoethanol) in pyridine with the main types of the reactive phosphorylating intermediates formed by treatment of pdT-Ac, pdTpdT-Ac, Tr-dTpdT-Ac, Tr-dTpdTpdT-Ac with 2,4,6-triisopropylbenzene-sulfonyl chloride (TPS): 1) B type derivatives with phosphomono ester (ME) group converted to a phosphoryl pyridinium residue; 2) C type derivatives with PME and phosphodiester (PDE) groups converted to trisubstituted pyrophosphate; 3) D type derivatives with PDE groups converted to tetrasubstituted pyrophosphate. The two latter types are partially present as cyclic intramolecular pyrophosphates Ci and Di. The reactivity of the intermediates decreases in the series B»Ci{approx}Di> C{approx}D. The Ci derivative of pdTpdT-Ac when obtained in dimethylformamide was found to be rather stable to hydrolysis and could be separated from the other dinucleotide derivatives by ion-exchange chromatography. The Arrhenius parameters of all steps of the conversion of PME group of pdT-Ac to B derivative and of the reaction of TPS with PDE group of dinucleoside phosphate Tr-dTpdT-Ac were measured.


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