Synthesis of a guanosine phosphoramidite derivative containing a photocleavable protecting group at the O6 position via regioselective protection of the 2'-hydroxy group with a TBDMS group.
To construct modified RNA that form A-type duplex with photo-irradiation, a photocleavable a-methyl-2-nitropiperonyl (MeNP) group was introduced at O(6) position of guanosine. A guanosine phosphoramidite derivative containing the MeNP group was synthesized via regioselective 2'-O-protection of 3',5'-O-di(t-butyl)silanediylguanosine with TBDMS group. The MeNP group was found to be stable under conditions of solid-phase synthesis of RNA. The MeNP group was also found to be removable by UV irradiation at wavelength of 365 nm for 10 min.
Iwase
Reiko
R
Department of Biosciences, Teikyo University of Science and Technology, 2525 Yatsusawa, Uenohara, Yamanashi 409-0193, Japan. iwase@ntu.ac.jp
Toyama
Takaaki
T
D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D016376:Oligonucleotides, Antisense / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D014466:Ultraviolet Rays
D016376:Oligonucleotides, Antisense; D006151:Guanosine; D012313:RNA