A novel method for the synthesis of DNA and its analogs by the use of BH3 as a protecting group for phosphonic acid.
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.
Kawanaka
Toshihide
T
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience building 702, Kashiwa, Chiba 277-8562, Japan.
Shimizu
Mamoru
M
Saigo
Kazuhiko
K
Wada
Takeshi
T
D001671:Biochemistry / Q000379:methods; D001880:Boranes / Q000737:chemistry*; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*
D001880:Boranes; D063065:Organophosphonates; D010710:Phosphates; C510710:boranophosphate; D004247:DNA