(R)-(+)-2-benzyl-2-methylsuccinic acid | 32980-47-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-(+)-2-benzyl-2-methylsuccinic acid
• 英文别名: (2R)-2-benzyl-2-methylbutanedioic acid
• CAS: 32980-47-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QFWZQNUAZRYHFF-GFCCVEGCSA-N

物化性质

• 熔点：
  144 °C(Solv: benzene (71-43-2))
• 沸点：
  338.4±22.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-methyl 2-benzyl-2-methyl-3-iodopropanoate 在 sodium hydroxide 、 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 34.0h， 生成 (R)-(+)-2-benzyl-2-methylsuccinic acid
  参考文献：
  名称：

  2-Benzyl-2-methylsuccinic acid as inhibitor for carboxypeptidase A. synthesis and evaluation

  摘要：

  Recently, Asante-Appiah et al. (Asante-Appiah, E.; Seetharaman, J.; Sicheri, F.; Yang, D. S.-C.; Chan, W. W.-C. Biochemistry 1997, 36, 8710-8715) reported that 2-ethyl-2-methylsuccinic acid isa highly potent inhibitor for carboxypeptidase A (CPA), a prototypic zinc protease. The X-ray crystal structure of the complex of the enzyme formed with 2-ethyl-2-methylsuccinic acid revealed that at the active site of CPA there is present a small cavity which accommodates the methyl group of the inhibitor. These investigators postulated that incorporation of a methyl group at the alpha-position to the carboxylate of existing inhibitors of CPA would improve the inhibitory potency. We have synthesized racemic and optically active 2-benzyl-2-methylsuccinic acids and evaluated their inhibitory activities for CPA to find the K-i values to be 0.28, 0.15, and 17 mu M for racemic form, (R)-, and (S)-enantiomer, respectively. Contrary to the expectation, the effect on the binding affinity by the incorporation of the methyl group is minimal. The validity of the proposition that the small cavity may be utilized for the improvement of the inhibitory potency appears questionable. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00110-8

文献信息

• Renin inhibitors containing phenylalanyl-histidine replacements
  申请人：Merck & Co., Inc.

  公开号：EP0278158A2

  公开（公告）日：1988-08-17

  Peptides of the formula: which comprise novel elements replacing the Phe(8)-His(9) sequence in renin-inhibitory peptides based on substrate analogy, which inhibit the substrate-cleaving action of renin and have improved bioavailability; compositions containing these renin-inhibitory peptides, optionally with other antihypertensive agents; and methods of treating hypertension or congestive heart failure or of establishing renin as a causative factor in these problems which employ the novel peptides.

  式中的肽，其包含的新型元素取代了基于底物类比的肾素抑制肽中的Phe(8)-His(9)序列，可抑制肾素的底物清除作用，并具有更好的生物利用度；含有这些肾素抑制肽的组合物，可选择与其他降压药一起使用；以及治疗高血压或充血性心力衰竭或确定肾素是这些问题的致病因素的方法，其中采用了新型肽。
• Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom
  作者：Fulvia Felluga、Franco Ghelfi、Giuliana Pitacco、Fabrizio Roncaglia、Ennio Valentin、Cesare Daniele Venneri

  DOI：10.1016/j.tetasy.2010.07.010

  日期：2010.9

  Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic beta,beta-dialkyl-gamma-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active gamma-nitroesters gave access to optically active beta,beta-disubstituted gamma-aminoacids as well as alpha,alpha-disubstituted succinic acids, both being biologically relevant compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• US4839357A
  申请人：——

  公开号：US4839357A

  公开（公告）日：1989-06-13
• US5039664A
  申请人：——

  公开号：US5039664A

  公开（公告）日：1991-08-13
• US5037807A
  申请人：——

  公开号：US5037807A

  公开（公告）日：1991-08-06