5-taurinomethyluridine | 497258-53-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-taurinomethyluridine
• 英文别名: 2-(((1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl)amino)ethanesulfonic acid；2-[[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]methylamino]ethanesulfonic acid
• CAS: 497258-53-4
• 化学式: C₁₂H₁₉N₃O₉S
• 分子量: 381.364
• InChiKey: VJKJOPUEUOTEBX-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  194
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-(羟甲基)-2',3'-O-(异丙亚基)尿苷 在 吡啶 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 38.5h， 生成 5-taurinomethyluridine
  参考文献：
  名称：

  Synthesis of various substituted 5-methyluridines (xm 5 U) and 2-thiouridines (xm 5 s 2 U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine

  摘要：

  5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm(5)U) and 5-methyl-2-thiouridines (xm(5)s(2)U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.023

文献信息

• Chemical Synthesis and Properties of 5-Taurinomethyluridine and 5-Taurinomethyl-2-thiouridine
  作者：Toshihiko Ogata、Tomomi Shimazaki、Tadashi Umemoto、Shinya Kurata、Takashi Ohtsuki、Tsutomu Suzuki、Takeshi Wada

  DOI：10.1021/jo802697r

  日期：2009.3.20

  Unique taurine-containing Uridine derivatives, 5-taurinomethyluridine (tau m(5)U) and 5-taurinomethyl-2-thiouridine (tau m(5)s(2)U), 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 m(5)U and tau m(5)s(2)U 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 H-1 NMR spectrometric studies revealed the structural properties of the taurine-containing base moieties and the Sugar conformations of these modified ribonucleosides.
• Synthesis of various substituted 5-methyluridines (xm 5 U) and 2-thiouridines (xm 5 s 2 U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine
  作者：Karolina Bartosik、Grazyna Leszczynska

  DOI：10.1016/j.tetlet.2015.10.023

  日期：2015.11

  5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm(5)U) and 5-methyl-2-thiouridines (xm(5)s(2)U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate. (C) 2015 Elsevier Ltd. All rights reserved.