Open AccessA novel method for the synthesis of DNA and its analogs by the use of BH3 as a protecting group for phosphonic acid
Author(s) -
Toshihide Kawanaka,
Mamoru Shimizu,
Kazuhiko Saigo,
Takeshi Wada
Publication year - 2005
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/49.1.27
Subject(s) - phosphonate , dna , chemistry , transformation (genetics) , combinatorial chemistry , protecting group , group (periodic table) , stereochemistry , reaction conditions , dna synthesis , organic chemistry , biochemistry , catalysis , gene , alkyl
Recently, we have developed a novel reaction for the transformation of boranophosphate diesters to the corresponding H-phosphonate diesters in the presence of trityl cation under acidic conditions. In this study, DNA and backbone-modified DNA analogs were synthesized in good yields upon applying this reaction. We report the transformation of boranophosphate DNAs, fully protected with 2-azidomethylbenzoyl groups, to various backbone-modified DNA analogs via the H-phosphonate intermediates in solution and on a solid support.
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