Chemical synthesis and properties of stereoregulated phosphorothioate RNAs.
Stereoregulated oligoribonucleoside phosphorothioates were synthesized by the use of 2'-O-TBDMS-protected ribonucleoside 3'-O-oxazaphospholidine derivatives as monomers and N-(cyanomethyl)ammonium salts as activators. Diastereoselectivity of the condensation reaction was found to be highly dependent on the substituent groups of the oxazaphospholidine ring as well as the structure of the activators. By the use of the optimized oxazaphospholidine monomers and activators, stereoregulated oligoribonucleoside phosphorothioates containing four kinds of nucleobases were synthesized in good yields. Hybridization properties of thus obtained oligomers with the complementary RNAs were evaluated by the UV melting experiments.
Wada
Takeshi
T
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan. wada@k.u-tokyo.ac.jp
Kondo
Tomoaki
T
Fujiwara
Satoshi
S
Sato
Terutoshi
T
Oka
Natsuhisa
N
D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D054735:Phosphorothioate Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D013237:Stereoisomerism
D009843:Oligoribonucleotides; D054735:Phosphorothioate Oligonucleotides; D012313:RNA