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Nucleic Acids Research, 1979, Vol. 7, No. 3 805-823
© 1979

Articles

Fluoride ion promoted deprotection and transesterification in nucleotide triesters

Kelvin K. Ogilvie and Serge L. Beaucage

Department of Chemistry, McGill University Montreal, Quebec H3A 2K6, Canada

Received April 16, 1979. Tetrabutylammonium fluoride will remove phenyl, trichloroethyl and cyanoethyl groups from nucleotides. In addition to the desired nucleotide products other results including chain cleavage, phosphofluoridates, and cyanoethylated thymidine units may be obtained depending on the conditions used. Fluoride ion has been used to successfully exchange phenyl and trichloroethyl groups for methyl, ethyl and butyl ghoups in nucleotide triesters. This represents a rapid high yield route to a variety of phosphate esters. The synthesis of a novel nucleotide analogue, in which two chains are bridged through their phosphates is described.


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