title: Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study.
abstract: [chemical reaction: see text]. We report here the synthesis of the 5'-[benzhydryloxybis(trimethylsilyloxy)]silyl-2'-methylseleno-2'-deoxyuridine phosphoramidite and its incorporation into oligonucleotides by solid-phase synthesis. The coupling yield of this phosphoramidite into oligonucleotides is higher than 99%. We also demonstrate that this 2'-methylselenophosphoramidite is compatible with the 5'-silyl-2'-ACE chemistry, for longer Se-RNA solid-phase synthesis. Our preliminary NMR study on the synthesized 2'-Se-DNA has revealed a U(Se)-A base pair and a duplex structure formation when its complementary strand was present.
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA.
authors.forename: Jozef
authors.initials: J
authors.lastname: Salon
authors.forename: Guexiong
authors.initials: G
authors.lastname: Chen
authors.forename: Yoani
authors.initials: Y
authors.lastname: Portilla
authors.forename: Markus W
authors.initials: MW
authors.lastname: Germann
authors.forename: Zhen
authors.initials: Z
authors.lastname: Huang
mesh_terms: D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: C512550:5'-(benzhydryloxybis(trimethylsilyloxy))silyl-2'-methylseleno-2'-deoxyuridine phosphoramidite; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D016566:Organoselenium Compounds; C101323:uridine phosphoramidite; D003857:Deoxyuridine; D014529:Uridine