Thiamine sulfide | 77609-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Thiamine sulfide
• 英文别名: thiamine；N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-1-methyl-2-thioxo-butyl)-formamide；N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-2-mercapto-1-methyl-but-1-en-t-yl)-formamide；N-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-2-mercapto-1-methyl-but-1-en-t-yl)-formamid；Thiamin-thiol；Thiaminthiol；(Z)-N-((4-Amino-2-methylpyrimidin-5-yl)methyl)-N-(5-hydroxy-3-mercaptopent-2-en-2-yl)formamide；N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-5-hydroxy-3-sulfanylpent-2-en-2-yl]formamide
• CAS: 77609-62-2
• 化学式: C₁₂H₁₈N₄O₂S
• 分子量: 282.367
• InChiKey: IDPJGITXELWXRN-FLIBITNWSA-N

物化性质

• 沸点：
  565.1±50.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Thiamine sulfide 在 盐酸 作用下， 生成 盐酸硫胺素杂质9
  参考文献：
  名称：

  Hydrolysis of thiamine

  摘要：

  The hydrolysis of thiamine has been studied over the range 0.5 < pH < 10.5 in aqueous solution at 25 degrees C using the stopped-flow technique. When the backward reaction from thiazolium anion to thiamine is followed, two relaxation effects are observed and the evaluation of the relaxation amplitudes allows us to determine seven independent equilibrium constants between thiamine, differently protonated pseudo bases and differently protonated thioles. The results are confirmed by the pH-dependence of the relaxation times. The hydrolysis of thiamine proceeds via the same mechanism as observed for other thiazolium salts, when the protonation of the pyrimidine ring of thiamine is also taken into account for all species.

  DOI：

  10.1039/p29950000463
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 生成 Thiamine sulfide
  参考文献：
  名称：

  Hydrolysis of thiamine

  摘要：

  The hydrolysis of thiamine has been studied over the range 0.5 < pH < 10.5 in aqueous solution at 25 degrees C using the stopped-flow technique. When the backward reaction from thiazolium anion to thiamine is followed, two relaxation effects are observed and the evaluation of the relaxation amplitudes allows us to determine seven independent equilibrium constants between thiamine, differently protonated pseudo bases and differently protonated thioles. The results are confirmed by the pH-dependence of the relaxation times. The hydrolysis of thiamine proceeds via the same mechanism as observed for other thiazolium salts, when the protonation of the pyrimidine ring of thiamine is also taken into account for all species.

  DOI：

  10.1039/p29950000463

文献信息

• Structures of Thiamine in Basic Solution¹
  作者：George D. Maier、David E. Metzler

  DOI：10.1021/ja01573a040

  日期：1957.8
• Yatco-Manzo et al., Journal of Biological Chemistry, 1959, vol. 234, p. 733,735, 736
  作者：Yatco-Manzo et al.

  DOI：——

  日期：——
• Watanabe; Asahi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1046
  作者：Watanabe、Asahi

  DOI：——

  日期：——
• [EN] APTAMERS THAT BIND THIAMINE ANALOGS AND DERIVATIVES<br/>[FR] APTAMÈRES QUI LIENT LES ANALOGUES ET DÉRIVÉS DE LA THIAMINE
  申请人：MEIRAGTX UK II LTD

  公开号：WO2021191680A1

  公开（公告）日：2021-09-30

  The present disclosure relates to oligonucleotide aptamers that bind to certain small molecules including thiamine analogs and derivatives and methods of generating aptamers that bind to the small molecules. Also contemplated are riboswitches and polynucleotide cassettes comprising the aptamers disclosed herein. Further provided are methods of using said aptamers, riboswitches, and/or polynucleotide for the regulation of target genes, including therapeutic genes. Also provided herein are small molecules that are modulators of target gene expression where the target gene contains a riboswitch comprising an aptamer described herein.
• Hydrolysis of thiamine
  作者：Joachim Herrmann、Wilhelm Knoche、Roland Neugebauer

  DOI：10.1039/p29950000463

  日期：——

  The hydrolysis of thiamine has been studied over the range 0.5 < pH < 10.5 in aqueous solution at 25 degrees C using the stopped-flow technique. When the backward reaction from thiazolium anion to thiamine is followed, two relaxation effects are observed and the evaluation of the relaxation amplitudes allows us to determine seven independent equilibrium constants between thiamine, differently protonated pseudo bases and differently protonated thioles. The results are confirmed by the pH-dependence of the relaxation times. The hydrolysis of thiamine proceeds via the same mechanism as observed for other thiazolium salts, when the protonation of the pyrimidine ring of thiamine is also taken into account for all species.