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Nucleic Acids Research, 1980, Vol. 8, No. 10 2301-2306
© 1980


Articles

The case of sulfonation in the chemical synthesis of oligonucleotides

A. Kraszewski, J. Stawinski and M. Wiewiórowski

Department of Stereochemistry of Natural Products, Institute of Organic Chemistry, Polish Academy of Sciences Noskowskiego 12/14, 61–704 Poznan, Poland

Received March 5, 1980.

The sulfonation of nucleosidic component, a side reaction during phosphotriester bond formation, as a function of the reactivity of the condensing agents and the kind of substituents in the starting phosphodiester is discussed. It was found that in the coupling reaction of nucleoside alkyl phosphodiesiers, the degree of sulfonation of the nucleosidic component was very high; while under the same conditions when the aryl group was present in the corresponding phosphodiester, this side reaction practically did not occur.


*For reaction condition see Experimental Section.


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