phosphoric acid mono-[2-(2,7-dimethyl-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidin-8-yl)-ethyl] ester | 13185-54-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: phosphoric acid mono-[2-(2,7-dimethyl-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidin-8-yl)-ethyl] ester
• 英文别名: 2-(6,12-Dimethyl-4-thia-2,7,11,13-tetrazatricyclo[7.4.0.03,7]trideca-1(13),2,5,9,11-pentaen-5-yl)ethyl dihydrogen phosphate
• CAS: 13185-54-1
• 化学式: C₁₂H₁₅N₄O₄PS
• 分子量: 342.315
• InChiKey: JXYCJFTYPJJCDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  醌肟腙 在 氢氧化钾 、 potassium acetate 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 0.02h， 生成 phosphoric acid mono-[2-(2,7-dimethyl-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidin-8-yl)-ethyl] ester
  参考文献：
  名称：

  Thiamin Biosynthesis in Eukaryotes:  Characterization of the Enzyme-Bound Product of Thiazole Synthase from Saccharomyces cerevisiae and Its Implications in Thiazole Biosynthesis

  摘要：

  The biosynthesis of thiamin pyrophosphate in eukaryotes is different from the prokaryotic biosynthesis and is poorly understood to date. Only one thiazole biosynthetic gene has been identified (Thi4 in Saccharomyces cerevisiae). Here we report the identification and characterization of a Thi4-bound metabolite that consists of the ADP adduct of 5-(2-hydroxyethyl)-4-methylthiazole-2-carboxylic acid. The unexpected structure of this compound yields the first insights into the mechanism of thiamin thiazole biosynthesis in eukaryotes.

  DOI：

  10.1021/ja061413o

文献信息

• ——
  作者：A. I. Vovk

  DOI：10.1023/a:1023361817590

  日期：——

  The kinetics of reduction of ferricytochrome c in its reaction with thiamine and its O-substituted structural analogs in phosphate buffer at pH 7.5-7.8 were studied. The reduction rate is proportional to the concentration of thiamine or its derivatives. The dependence of the reaction rate on the oxidant concentration is characterized by negative deviations from linearity. In oxidation with ferricytochrome c, the reactivity of thiamine consdierably exceeds the reactivity of thiamine diphosphate and thiamine monophosphate, and in oxidation with ferricyanide the reaction rate increases in the order thiamine monophosphate < thiamine < thiamine diphosphate. With O-(2-norbornoyl)thiamine, O-(2-adamantyl)acetylthiamine, O-benzoylthiamine, O-(4-nitrobenzoyl)thiamine, or O-(5-nitro-2-chlorobenzoyl)thiamine, the rate of ferricytochrome c reduction is higher than with thiamine. Presumably, the electron transfer to the heme group of the oxidant is preceded by formation of a complex of ferricytochrome c with the neutral tricyclic form of the substrate.
• Hazra, Amrita; Chatterjee, Abhishek; Begley, Tadhg P., Journal of the American Chemical Society, 2009, vol. 131, p. 3225 - 3229
  作者：Hazra, Amrita、Chatterjee, Abhishek、Begley, Tadhg P.

  DOI：——

  日期：——
• Thiamin Biosynthesis in Eukaryotes:  Characterization of the Enzyme-Bound Product of Thiazole Synthase from <i>Saccharomyces </i><i>c</i><i>erevisiae </i>and Its Implications in Thiazole Biosynthesis
  作者：Abhishek Chatterjee、Christopher T. Jurgenson、Frank C. Schroeder、Steven E. Ealick、Tadhg P. Begley

  DOI：10.1021/ja061413o

  日期：2006.6.1

  The biosynthesis of thiamin pyrophosphate in eukaryotes is different from the prokaryotic biosynthesis and is poorly understood to date. Only one thiazole biosynthetic gene has been identified (Thi4 in Saccharomyces cerevisiae). Here we report the identification and characterization of a Thi4-bound metabolite that consists of the ADP adduct of 5-(2-hydroxyethyl)-4-methylthiazole-2-carboxylic acid. The unexpected structure of this compound yields the first insights into the mechanism of thiamin thiazole biosynthesis in eukaryotes.