Open AccessFluoride ion catalyzed alkylation of purines, pyrimidines, nucleosides and nucleotides using alkyl halides
Author(s) -
Kelvin K. Ogilvie,
Serge L. Beaucage,
Michael F. Gillen,
Douglas W. Entwistle,
Michael A. Quilliam
Publication year - 1979
Publication title -
nucleic acids research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.008
H-Index - 537
eISSN - 1362-4954
pISSN - 0305-1048
DOI - 10.1093/nar/6.4.1695
Subject(s) - alkylation , halide , nucleoside , nucleotide , alkyl , purine metabolism , thymidine , fluoride , phosphate , purine , base (topology) , biology , chemistry , catalysis , stereochemistry , organic chemistry , biochemistry , dna , inorganic chemistry , gene , mathematical analysis , mathematics , enzyme
Alkyl halides react rapidly with purines and pyrimidines in the presence of fluoride ion. Alkylation of thymidine leads to novel dimeric nucleoside derivatives bridged through N3. Alkylation of thymidine mono and dinucleotides leads to alkylation at the base (N3) as well as diester and triester formation at the phosphate.