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Nucleic Acids Research, 1985, Vol. 13, No. 7 2469-2484
© 1985

Articles

Oligomerization of activated derivatives of 3'-amino-3'-deoxyguanosine on poly(C) and poly(dC) templates

Wojciech S. Zielinski and Leslie E. Orgel

The Salk Institute for Biological Studies P.O. Box 85800, San Diego, CA 92138, USA

Received January 22, 1985. Revised March 11, 1985. Accepted March 15, 1985.

3'-amino-3'-deoxyuridine reacts with the nudeoside 5'-phosphorimidazolides in aqueous solution to give dinucleoside phosphoramidates. The reactions are one to two orders of magnitude faster than the corresponding reactions of uridine.

In the presence of poly(C) or poly(dC) it is known that guanosine-5'-phosphorimidazolide does not condense efficiently or regiospecifically. However, the introduction of a methyl group at the 2-position of the imidazole ring leads to efficient synthesis of long 3'-5'-linked oligomers. The corresponding imidazole derivatives of 3'-amino-3'-deoxyguanosine-5'-phosphate both condense on these templates to give virtually identical families of products. Our results suggest that the intrinsically greater nucleophilicity of the amine groups will permit a much wider range of efficient template-directed syntheses with 3'-amino-3'-deoxynucleoside derivatives than with the corresponding derivatives of the parent nucleosides.


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