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Nucleic Acids Research, 1975, Vol. 2, No. 6 773-786
© 1975

Articles

Solid support synthesis of ollgothymidylates using phosphorochloridates and 1-alkylimidazoles

Reynaldo C. Pless and Robert L. Letsinger

Department of Chemistry, Northwestern University Evanston, Illinois 60201, USA

Received February 26, 1975. A study of the synthesis of oligothymidylates via phosphotriester intermediates on a polystyrene support is described. The sequence involves condensation of a phenyl nucleoside-3'-phosphorochloridate with the 5'-hydroxyl group of the carrier bound oligonucleotide derivative in the presence of 1-methylimidazole. Conditions for preparation of the phenyl nucleoside phosphorochloridate as well as for the condensation on the support are discussed. d-TpTpTpT was obtained in 31% overall yield from carrier bound thymidine in one series of experiments, and d-TpTpTpTpT was obtained in 9% yield in another. The cycle for addition of one nucleotide unit can be completed in about six hours.


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