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...

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Published inNucleic acids symposium series (2004) no. 51; pp. 135 - 136
Main Authors Iwase, Reiko, Toyama, Takaaki
Format Journal Article
LanguageEnglish
Published England 2007
Subjects
Guanosine - analogs & derivatives
Guanosine - chemical synthesis
Guanosine - chemistry
Guanosine - radiation effects
Oligonucleotides, Antisense - chemistry
RNA - chemical synthesis
RNA - chemistry
RNA - radiation effects
Ultraviolet Rays
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Summary: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.
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ISSN:1746-8272