title: Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine.
abstract: Unique taurine-containing uridine derivatives, 5-taurinomethyluridine (tau m5U) and 5-taurinomethyl-2-thiouridine (tau m5s2U), which were discovered in mammalian mitochondrial tRNAs, exist at the first position of the anticodon. In this paper, we report the first efficient synthesis of tau m5U and tau m5s2U and describe their physicochemical properties. These modified ribonucleosides were synthesized by the reaction of 5-substituted uridine derivatives with a tetrabutylammonium salt of taurine that is highly reactive and well-soluble in common organic solvents. UV and 1H NMR spectrometric studies revealed the structural properties of the taurine-containing base moieties and the sugar conformations of these modified ribonucleosides.
authors.affiliation: Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Ogata
authors.forename: Tomomi
authors.initials: T
authors.lastname: Shimazaki
authors.forename: Tadashi
authors.initials: T
authors.lastname: Umemoto
authors.forename: Shinya
authors.initials: S
authors.lastname: Kurata
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohtsuki
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Suzuki
authors.forename: Takeshi
authors.initials: T
authors.lastname: Wada
mesh_terms: D015394:Molecular Structure; D013057:Spectrum Analysis; D013654:Taurine / Q000737:chemistry; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C105273:2-thiouridine; C540247:5-taurinomethyl-2-thiouridine; C522070:5-taurinomethyluridine; D013891:Thiouridine; D013654:Taurine; D014529:Uridine