semisuccinaldehyde hydrate

• 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: semisuccinaldehyde hydrate
• 英文别名: dihydroxybutanoic acid；4-Dihydroxybutanoic acid；4,4-dihydroxybutanoic acid
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: VLZDQMVCSFFDNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基半胱胺 、 琥珀半醛 、 semisuccinaldehyde hydrate 在 potassium phosphate 作用下， 以 水 、 重水 为溶剂， 生成
  参考文献：
  名称：

  Coenzyme A Hemithioacetals as Easily Prepared Inhibitors of CoA Ester-Utilizing Enzymes

  摘要：

  Hemithioacetals are formed by reactions of coenzyme A (CoA) with aldehydes in aqueous solution. Equilibria for hemithioacetal formation with four commercially available aldehydes and rate constants for hemithioacetal dissociation have been studied. The hemithioacetals are viewed as acyl-CoA analogs having a tetrahedral center in place of the planar trigonal thioester carbonyl carbon. These compounds may serve as mimics of the tetrahedral intermediate or transition state in the reactions of acyl-CoA dependent acyltransferase enzymes. The hemithioacetal generated by reaction of CoA with formaldehyde is a poor inhibitor of chloramphenicol acetyltransferase, with a K-i more than B-fold higher than the K-m for the substrate acetyl-CoA. The hemithioacetals formed by reaction of CoA with acetaldehyde and trifluroacetaldehyde are substantially better inhibitors, with K-i values approximately 2.4-fold and 10-fold lower than the K-m values for acetyl-CoA, respectively. The hemithioacetal formed by reaction of CoA with succinic semialdehyde inhibits succinic thiokinase, with a K-i 4-fold lower than the K-m for the substrate succinyl-CoA. The CoA hemithioacetals provide a novel readily accessible new class of acyl-CoA analogs for use in mechanistic and structural studies of CoA ester-utilizing enzymes.

  DOI：

  10.1021/jo9616724
• 作为产物：
  描述：

  在 potassium phosphate 作用下， 以 水 、 重水 为溶剂， 生成 N-乙酰基半胱胺 、 琥珀半醛 、 semisuccinaldehyde hydrate
  参考文献：
  名称：

  Coenzyme A Hemithioacetals as Easily Prepared Inhibitors of CoA Ester-Utilizing Enzymes

  摘要：

  Hemithioacetals are formed by reactions of coenzyme A (CoA) with aldehydes in aqueous solution. Equilibria for hemithioacetal formation with four commercially available aldehydes and rate constants for hemithioacetal dissociation have been studied. The hemithioacetals are viewed as acyl-CoA analogs having a tetrahedral center in place of the planar trigonal thioester carbonyl carbon. These compounds may serve as mimics of the tetrahedral intermediate or transition state in the reactions of acyl-CoA dependent acyltransferase enzymes. The hemithioacetal generated by reaction of CoA with formaldehyde is a poor inhibitor of chloramphenicol acetyltransferase, with a K-i more than B-fold higher than the K-m for the substrate acetyl-CoA. The hemithioacetals formed by reaction of CoA with acetaldehyde and trifluroacetaldehyde are substantially better inhibitors, with K-i values approximately 2.4-fold and 10-fold lower than the K-m values for acetyl-CoA, respectively. The hemithioacetal formed by reaction of CoA with succinic semialdehyde inhibits succinic thiokinase, with a K-i 4-fold lower than the K-m for the substrate succinyl-CoA. The CoA hemithioacetals provide a novel readily accessible new class of acyl-CoA analogs for use in mechanistic and structural studies of CoA ester-utilizing enzymes.

  DOI：

  10.1021/jo9616724

文献信息

• Coenzyme A Hemithioacetals as Easily Prepared Inhibitors of CoA Ester-Utilizing Enzymes
  作者：Benjamin Schwartz、Kurt W. Vogel、Dale G. Drueckhammer

  DOI：10.1021/jo9616724

  日期：1996.1.1

  Hemithioacetals are formed by reactions of coenzyme A (CoA) with aldehydes in aqueous solution. Equilibria for hemithioacetal formation with four commercially available aldehydes and rate constants for hemithioacetal dissociation have been studied. The hemithioacetals are viewed as acyl-CoA analogs having a tetrahedral center in place of the planar trigonal thioester carbonyl carbon. These compounds may serve as mimics of the tetrahedral intermediate or transition state in the reactions of acyl-CoA dependent acyltransferase enzymes. The hemithioacetal generated by reaction of CoA with formaldehyde is a poor inhibitor of chloramphenicol acetyltransferase, with a K-i more than B-fold higher than the K-m for the substrate acetyl-CoA. The hemithioacetals formed by reaction of CoA with acetaldehyde and trifluroacetaldehyde are substantially better inhibitors, with K-i values approximately 2.4-fold and 10-fold lower than the K-m values for acetyl-CoA, respectively. The hemithioacetal formed by reaction of CoA with succinic semialdehyde inhibits succinic thiokinase, with a K-i 4-fold lower than the K-m for the substrate succinyl-CoA. The CoA hemithioacetals provide a novel readily accessible new class of acyl-CoA analogs for use in mechanistic and structural studies of CoA ester-utilizing enzymes.