Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions.
Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.
Ohkubo
Akihiro
A
Department of Life Science, Tokyo Institute of Technology, J2-12, 4259 Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Kuwayama
Yasukazu
Y
Nishino
Yudai
Y
Tsunoda
Hirosuke
H
Seio
Kohji
K
Sekine
Mitsuo
M
D000578:Amidines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry
D000578:Amidines; D009841:Oligonucleotides; D012313:RNA