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

Toshihiko Ogata, Tomomi Shimazaki, Tadashi Umemoto, Shinya Kurata, Takashi Ohtsuki, Tsutomu Suzuki, Takeshi Wada

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Unique taurine-containing uridine derivatives, 5-taurinomethyluridine (τm5U) and 5-taurinomethyl-2-thiouridine (τm 5S2U), 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 τm5U and τm 5S2U 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 wellsoluble 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.

Original languageEnglish
Pages (from-to)2585-2588
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number6
DOIs
Publication statusPublished - Mar 20 2009
Externally publishedYes

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Taurine
Ribonucleosides
Uridine
Derivatives
Anticodon
Transfer RNA
Sugars
Organic solvents
Conformations
Structural properties
Salts
Nuclear magnetic resonance
5-taurinomethyluridine
5-taurinomethyl-2-thiouridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. / Ogata, Toshihiko; Shimazaki, Tomomi; Umemoto, Tadashi; Kurata, Shinya; Ohtsuki, Takashi; Suzuki, Tsutomu; Wada, Takeshi.

In: Journal of Organic Chemistry, Vol. 74, No. 6, 20.03.2009, p. 2585-2588.

Research output: Contribution to journalArticle

Ogata, Toshihiko ; Shimazaki, Tomomi ; Umemoto, Tadashi ; Kurata, Shinya ; Ohtsuki, Takashi ; Suzuki, Tsutomu ; Wada, Takeshi. / Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 6. pp. 2585-2588.
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