BIOMAT Database Logo BIOMAT Database Logo

Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. 2009

Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.

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.

UI MeSH Term Description Entries
D013057 Spectrum Analysis The measurement of the amplitude of the components of a complex waveform throughout the frequency range of the waveform. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Spectroscopy,Analysis, Spectrum,Spectrometry
D013654 Taurine A conditionally essential nutrient, important during mammalian development. It is present in milk but is isolated mostly from ox bile and strongly conjugates bile acids. Taufon,Tauphon,Taurine Hydrochloride,Taurine Zinc Salt (2:1),Taurine, Monopotassium Salt
D013891 Thiouridine A photoactivable URIDINE analog that is used as an affinity label. 4-Thiouridine,4 Thiouridine
D014529 Uridine A ribonucleoside in which RIBOSE is linked to URACIL. Allo-Uridine,Allouridine,Allo Uridine
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Chemical synthesis of RNA including 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine.
January 2008, Nucleic acids symposium series (2004),
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Chemical synthesis of RNA including 5-taurinomethyluridine.
January 2006, Nucleic acids symposium series (2004),
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine.
August 2000, Bioorganic & medicinal chemistry letters,
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Synthesis and properties of 2'-O-alkylated 2-thiouridine derivatives and oligonucleotides containing 2'-O-alkylated 2-thiouridine derivatives.
January 2003, Nucleic acids research. Supplement (2001),
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Synthesis and properties of oligonucleotides containing 2'-O-methyl-2-thiouridine.
January 1999, Nucleic acids symposium series,
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
[On the synthesis and properties of 4-thiouridylyl-(3'-5')-4-thiouridine, 4-thiouridylyl-(3'-5')-uridine and uridylyl-(3'-5')-4-thiouridine].
September 1968, Biochimica et biophysica acta,
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
[The synthesis of 4-thiouridine-5'-diphosphate, 4-thiouridine-5'-triphosphate and desoxy-4-thiothymidine-5'-triphosphate].
January 1968, Chemische Berichte,
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
The preparation and properties of 4-thiouridine containing 2'-5' and 3'-5' dinucleoside monophosphates.
December 1975, Nucleic acids research,
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Synthesis of 5-methylaminomethyl-2-thiouridine, a rare nucleoside from t-RNA.
April 1975, Angewandte Chemie (International ed. in English),
Toshihiko Ogata, and Tomomi Shimazaki, and Tadashi Umemoto, and Shinya Kurata, and Takashi Ohtsuki, and Tsutomu Suzuki, and Takeshi Wada
Synthesis of Geranyl-2-Thiouridine-Modified RNA.
March 2017, Current protocols in nucleic acid chemistry,
Copied contents to your clipboard!