title: Synthesis of 5'-terminal capped oligonucleotides using O-N phosphoryl migration of phosphoramidite derivatives.
abstract: Trivalent phosphoramidite derivatives could be readily converted by reacting with 1-hydroxy-7-azabenzotriazole to phosphotriester intermediates; these intermediates reacted smoothly with phosphorylated compounds to give pyrophosphate derivatives. This new phosphorylation approach enabled a facile and rapid synthesis of 5'-adenylated DNA oligomers (A(5')ppDNA) on resins using a silyl-type linker. Our new approach could be applied to the synthesis of a 2'-OMe-RNA oligomer containing the 5'-terminal 2,2,7-trimethylguanosine cap structure.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Tago
authors.forename: Akira
authors.initials: A
authors.lastname: Yokouchi
authors.forename: Yudai
authors.initials: Y
authors.lastname: Nishino
authors.forename: Ken
authors.initials: K
authors.lastname: Yamada
authors.forename: Hirosuke
authors.initials: H
authors.lastname: Tsunoda
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010766:Phosphorylation
chemical_list: D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite