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Nucleic Acids Research, 1983, Vol. 11, No. 18 6513-6529
© 1983

CHEMISTRY

Derivatization of unprotected polynucleotides

Barbara C.F. Chu, Geoffrey M. Wahl and Leslie E. Orgel

The Salk Institute for Biological Studies San Diego, CA 92138, USA

Received June 9, 1983. Revised September 2, 1983. Accepted September 2, 1983.

A simple and efficient method for attaching amines to the terminal 51-phosphate of unprotected oligonucleotides or nucleic acids in aqueous solution is described. The method is applicable to low molecular-weight amines,polypeptides, or proteins.

The terminal 5'-phosphate of an oligonucleotide or nucleic acid reacts with a water-soluble carbodiimide in imidazole buffer at pH 6 to give good yields of the 5'-phosphorimidazolide. Exposure of the phosphorimidazolide to amine-containing molecules in aqueous solution results in the production of a wide range of stable phosphoramidates in high yield.

The exposure of polynucleotides to carbodiimide does not result in significant breakage of phosphodiester bonds or damage to nucleoside bases. The biological activity of a drug resistant plasmid is not affected.

The direct condensation of polynucleotidea with amines in 1-methylim-idazole buffer is also possible. However, it is not a satisfactory preparative method if the ligand is sensitive to carbodiimide.


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