(+)-(S)-3-Benzyl-2-oxetanone | 462118-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(S)-3-Benzyl-2-oxetanone
• 英文别名: (3S)-3-benzyloxetan-2-one
• CAS: 462118-49-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: ISVWQTQCIQCLOZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-3-Benzyl-2-oxetanone 在 Tris buffer 、 α-chymotrypsin 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-2-benzyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6
• 作为产物：
  描述：

  2-苄基-3-羟基丙酸甲酯 在 sodium hydroxide 、 phosphate buffer 、 dimethyl azodicarboxylate 、 三苯基膦 、 α-chymotrypsin 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 (+)-(S)-3-Benzyl-2-oxetanone
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6

文献信息

• LACTONE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20170313669A1

  公开（公告）日：2017-11-02

  Provided herein are lactone compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as inhibitors of serine hydrolases, such as ABHD16A. Furthermore, the subject compounds and compositions may be useful for the treatment of, for example, PHARC and other neuroinflammatory diseases.
• Cleavage of β-lactone ring by serine protease. Mechanistic implications
  作者：Dong H. Kim、Jeong-il Park、Sang J. Chung、Jung Dae Park、No-Kyung Park、Jong Hoon Han

  DOI：10.1016/s0968-0896(02)00108-6

  日期：2002.8

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.