tris(methylthio)methyldethia-CoA | 205325-77-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: tris(methylthio)methyldethia-CoA
• 英文别名: Adenosine 5a(2)-(trihydrogen diphosphate), 3a(2)-(dihydrogen phosphate), Pa(2)-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[[4,4,4-tris(methylthio)butyl]amino]propyl]amino]butyl] ester；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[4,4,4-tris(methylsulfanyl)butylamino]propyl]amino]butyl] hydrogen phosphate
• CAS: 205325-77-5
• 化学式: C₂₆H₄₆N₇O₁₆P₃S₃
• 分子量: 901.808
• InChiKey: PCOSZDHVCXDTPU-DJVIHCHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  55.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  346.56
• 氢给体数：
  9.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  tris(methylthio)methyldethia-CoA 在 盐酸 、 sodium hydroxide 、 potassium phosphate buffer 作用下， 反应 22.0h， 生成 (carboxymethylthio)carbonyldethia-CoA
  参考文献：
  名称：

  A Reversed Thioester Analogue of Acetyl-Coenzyme A:  An Inhibitor of Thiolase and a Synthon for Other Acyl-CoA Analogues

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) and CoA esters using a combination of enzymatic and nonenzymatic reactions (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660). We report here the extension of this method to a CoA ester analogue 1c in which the orientation of the thioester is reversed. A key to this synthesis is the use of a trithioortho ester as a protected thioester. The reversed thioester analogue Ic is a time-dependent inhibitor of thiolase, apparently forming an acyl enzyme in which the CoA moiety rather than an acetyl moiety is covalently attached to an active site nucleophile. This analogue also serves as a general synthon for analogues having other functionality at the site of the thioester group. This has been applied to the synthesis of a reversed thioester analogue of succinyl-CoA 6 and hydroxamate 7 and hydrazide 8 analogues of acetyl-CoA, analogues which are not available by the previously described methodology. The hydroxamate and hydrazide analogues are potent inhibitors of the enzyme citrate synthase. The reversed thioester analogue of acetyl-CoA may have useful applications in enzymology and permits the ready access to a range of additional CoA analogues modified in the thioester moiety.

  DOI：

  10.1021/ja971758u
• 作为产物：
  描述：

  4-azido-1,1,1-tris(methylsulfanyl)butane 在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 20.0h， 生成 tris(methylthio)methyldethia-CoA
  参考文献：
  名称：

  A Reversed Thioester Analogue of Acetyl-Coenzyme A:  An Inhibitor of Thiolase and a Synthon for Other Acyl-CoA Analogues

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) and CoA esters using a combination of enzymatic and nonenzymatic reactions (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660). We report here the extension of this method to a CoA ester analogue 1c in which the orientation of the thioester is reversed. A key to this synthesis is the use of a trithioortho ester as a protected thioester. The reversed thioester analogue Ic is a time-dependent inhibitor of thiolase, apparently forming an acyl enzyme in which the CoA moiety rather than an acetyl moiety is covalently attached to an active site nucleophile. This analogue also serves as a general synthon for analogues having other functionality at the site of the thioester group. This has been applied to the synthesis of a reversed thioester analogue of succinyl-CoA 6 and hydroxamate 7 and hydrazide 8 analogues of acetyl-CoA, analogues which are not available by the previously described methodology. The hydroxamate and hydrazide analogues are potent inhibitors of the enzyme citrate synthase. The reversed thioester analogue of acetyl-CoA may have useful applications in enzymology and permits the ready access to a range of additional CoA analogues modified in the thioester moiety.

  DOI：

  10.1021/ja971758u