Pre-activation strategy for oligodeoxyribonucleotide synthesis using triaryloxydichlorophosphoranes in the phosphotriester method.
Triaryloxydichlorophosphoranes were tested as condensing agents for oligodeoxyribonucleotide synthesis in the phosphotriester method. Tris(2,4,6-tribromophenoxy)dichlorophosphorane (BDCP) was found to be a relatively stable crystalline material which could be used as a chemical reagent. A notable feature of the BDCP-promoted condensation reaction was studied by 31P-NMR. A small amount of BDCP compared to the conventional condensing agent was effective for the generation of active nucleotide intermediates and BDCP itself was quantitatively converted into an inert material, tris(2,4,6-tribromophenyl)phosphate (2). Thus, BDCP enabled us to separate the activation step from the condensation process in the phosphotriester method. This preactivation method was applied to the solid-phase synthesis.
Hotoda
H
H
Department of Life Chemistry, Tokyo Institute of Technology, Yokohama, Japan.
Wada
T
T
Sekine
M
M
Hata
T
T
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D010758:Phosphorus
D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C027903:oligo (dT); C060627:tris(2,4,6-tribromophenoxy)dichlorophosphorane; D010758:Phosphorus