3-甲基-2-[(2-苯基乙酰基)氨基]戊酸 | 2752-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-甲基-2-[(2-苯基乙酰基)氨基]戊酸
• 英文名称: N-PhAc-α-isoleucine
• 英文别名: N-phenylacetylisoleucine；N-(Phenylacetyl)isoleucine；3-methyl-2-[(2-phenylacetyl)amino]pentanoic acid
• CAS: 2752-52-5
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD09806195
• 分子量: 249.31
• InChiKey: ZULOUGGNZOVTOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲基-2-[(2-苯基乙酰基)氨基]戊酸 在 penicillin G acylase from Achromobacter sp. CCM 4824 、 水 作用下， 生成 L-别异亮氨酸
  参考文献：
  名称：

  Resolution of α/β-amino acids by enantioselective penicillin G acylase from Achromobacter sp .

  摘要：

  Penicillin G acylases (PGAs) are enantioselective enzymes catalyzing a hydrolysis of stable amide bond in a broad spectrum of substrates. Among them, derivatives of alpha- and beta-amino acids represent a class of compounds with high application potential. PGA(Ec) from Escherichia coil and PGA(A) from Achromobacter sp. CCM 4824 were used to catalyze enantioselective hydrolyses of seven selected N-phenylacetylated alpha/beta-amino acid racemates. The PGA(A) showed higher stereoselectivity for enantiomers of N-PhA-beta-homoleucine, N-PhAc-alpha-tert-leucine and N-PhAc-beta-leucine. To study the mechanism of enantiodiscrimination on molecular level, we have constructed a homology model of PGA(A) that was used in molecular docking experiments with the same substrates. In-silico experiments successfully reproduced the data from experimental enzymatic resolutions confirming validity of employed modeling protocol. We employed this protocol to evaluate enantiopreference of PGA(A) towards seven new substrates with application potential. For five of them, high enantioselectivity of PGA(A) was predicted. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.09.008
• 作为产物：
  描述：

  isoleucine 、 苯乙酰氯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 生成 3-甲基-2-[(2-苯基乙酰基)氨基]戊酸
  参考文献：
  名称：

  Resolution of α/β-amino acids by enantioselective penicillin G acylase from Achromobacter sp .

  摘要：

  Penicillin G acylases (PGAs) are enantioselective enzymes catalyzing a hydrolysis of stable amide bond in a broad spectrum of substrates. Among them, derivatives of alpha- and beta-amino acids represent a class of compounds with high application potential. PGA(Ec) from Escherichia coil and PGA(A) from Achromobacter sp. CCM 4824 were used to catalyze enantioselective hydrolyses of seven selected N-phenylacetylated alpha/beta-amino acid racemates. The PGA(A) showed higher stereoselectivity for enantiomers of N-PhA-beta-homoleucine, N-PhAc-alpha-tert-leucine and N-PhAc-beta-leucine. To study the mechanism of enantiodiscrimination on molecular level, we have constructed a homology model of PGA(A) that was used in molecular docking experiments with the same substrates. In-silico experiments successfully reproduced the data from experimental enzymatic resolutions confirming validity of employed modeling protocol. We employed this protocol to evaluate enantiopreference of PGA(A) towards seven new substrates with application potential. For five of them, high enantioselectivity of PGA(A) was predicted. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.09.008

文献信息

• Indoline compounds as granzyme B inhibitors
  申请人：viDA Therapeutics Inc.

  公开号：US10329324B2

  公开（公告）日：2019-06-25

  Granzyme B inhibitor compounds, compositions that include the compounds, and methods for using the compounds. The compounds of the invention have advantageous water solubility and effectively inhibit Granzyme B.

  Granzyme B 抑制剂化合物、包括这些化合物的组合物以及使用这些化合物的方法。本发明的化合物具有良好的水溶性，能有效抑制 Granzyme B。
• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0226304B1

  公开（公告）日：1991-08-28
• INDOLINE COMPOUNDS AS GRANZYME B INHIBITORS
  申请人：viDA Therapeutics Inc.

  公开号：US20180057528A1

  公开（公告）日：2018-03-01

  Granzyme B inhibitor compounds, compositions that include the compounds, and methods for using the compounds. The compounds of the invention have advantageous water solubility and effectively inhibit Granzyme B.
• US4757066A
  申请人：——

  公开号：US4757066A

  公开（公告）日：1988-07-12