Chemical synthesis of H-phosphonate DNA without using N-protecting groups.
Oligodeoxyribonucleotides were synthesized by using N-unprotected H-phosphonate monomers. It was found that the amino groups of nucleosides were not modified during condensation where benzotriazolyloxy carbonium and phosphonium types of compounds were employed as condensing reagents. The most effective condensing reagent for rapid internucleotidic bond formation was found to be 2-(benzotriazol-1-yloxy)-1,1-dimethyl-2-(pyrrolidin-1- yl)-1,3,2- diazaphospholidinium hexafluorophosphate (BOMP). In the present H-phosphonate approach, 2-benzenesulfonyl-3-(3-nitrophenyl)oxaziridine (BNO) was successfully employed as a new oxidizing reagent for oxidation of the H-phosphonate linkages under anhydrous conditions.
Wada
T
T
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Honda
F
F
Sato
Y
Y
Kawahara
S
S
Sekine
M
M
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates
D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D063065:Organophosphonates; D004247:DNA