2-hydroxy-2-<(methylthio)methyl>butanedioic acid | 144373-33-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxy-2-<(methylthio)methyl>butanedioic acid
• 英文别名: 2-Hydroxy-2-(methylsulfanylmethyl)butanedioic acid
• CAS: 144373-33-1
• 化学式: C₆H₁₀O₅S
• 分子量: 194.208
• InChiKey: BVIHJOJECQSKCX-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±42.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-<(methylthio)methyl>butanedioic acid 在 oil scarlet 、 2,4,6-三甲基苯磺酰羟胺 、 potassium carbonate 、 臭氧 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 -4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ4-isothiazole-4-acetic acid benzyl ester
  参考文献：
  名称：

  ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors

  摘要：

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.

  DOI：

  10.1021/jm00104a014
• 作为产物：
  描述：

  4-(methylthio)-3-oxobutanoic acid methyl ester 以68%的产率得到
  参考文献：
  名称：

  Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884

  摘要：

  DOI：

文献信息

• Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884
  作者：Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+

  DOI：——

  日期：——
• ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors
  作者：Roland E. Dolle、David McNair、Mark J. Hughes、Lawrence I. Kruse、Drake Eggelston、Barbara A. Saxty、Timothy N. C. Wells、Pieter H. E. Groot

  DOI：10.1021/jm00104a014

  日期：1992.12

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.