title: Synthesis of 8-oxoguanosine phosphoramidite and its incorporation into Oligoribonucleotides..
abstract: The detailed synthetic protocol for preparation of the phosphoramidite of an oxidatively damaged ribonucleotide, 8-oxoguanosine (8-oxo-G), and its incorporation into RNA are described. The O(6)- and N(7)-bisdiphenylcarbamoyl-protected 8-oxoguanosine phosphoramidite was synthesized as a new phosphoramidite precursor unit for the synthesis of RNA. It was successfully incorporated into the RNA sequences, and the synthesized RNAs were completely deprotected with 28% aqueous ammonia solution at 55°C for 24 hr. After purification using HPLC, they were identified by MALDI-TOF mass measurement. The base-pairing properties showed that 8-oxo-G forms base pairs not only with rC or dC in anti-conformation, but also with rA in syn conformation within the RNA duplexes or RNA/DNA heteroduplexes.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi, Higashi-ku, Fukuoka, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Taniguchi
authors.forename: Yohei
authors.initials: Y
authors.lastname: Koga
authors.forename: Shigeki
authors.initials: S
authors.lastname: Sasaki
mesh_terms: D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification*
chemical_list: D009843:Oligoribonucleotides; D006151:Guanosine; C046215:8-hydroxyguanosine
keywords: 8‐oxoguanosine; base pairing; oxidatively damaged ribonucleotide