Nucleosidic phosphorylating agent and methods

Details Nucleosidic phosphorylating agent and methods Nucleosidic phosphorylating agent and methods

1979-12-26

1982-01-12

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 22, 536 28, 536 29, C07H 1910, C07H 1916, C07H 2100

Patent

active

043106625

ABSTRACT:
Compounds of the formula ##STR1## where R is a base labile substituted-phenyloxy protecting group, are useful as phosphorylating reagents in the synthesis of oligonucleotides by a phosphotriester method. Such compounds are made by the reaction of .beta.-cyanoethanol and a corresponding R-phosphorodichloridate. A method of phosphorylating involves reacting such compounds, in the presence of base, with a nucleoside or a polynucleotide having a free 3' hydroxyl group, having the 5'--0 position protected by an organic group labile in acidic medium and having any phosphotriester linking groups protected by an organic group labile in strong basic medium.

REFERENCES:
Chemical Abstracts, vol. 90, p. 148056, Crea, R., et al., No. 148062, "Chemical Synthesis of Genes for Human Insulin," Proc. Natl. Acad. Sci. U.S.A., 75(12), 5765-5769, 1978.
Itakura, K., et al., Can. J. Chem., vol. 51, pp. 3649-3651, 1973.
Crea et al., Proceedings of The National Academy of Science, vol. 75, pp. 5765-5769, 1978.

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