Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study.
[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.
Salon
Jozef
J
Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA.
Chen
Guexiong
G
Portilla
Yoani
Y
Germann
Markus W
MW
Huang
Zhen
Z
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
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