N-2-(3-phenylpropionyl)-α-amino-2-methylpropionic acid | 409108-29-8

• 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
• 英文名称: N-2-(3-phenylpropionyl)-α-amino-2-methylpropionic acid
• 英文别名: 2-(3-phenyl-propanoyl-amino)-isobutyric acid；Alanine, 2-methyl-N-(1-oxo-3-phenylpropyl)-；2-methyl-2-(3-phenylpropanoylamino)propanoic acid
• CAS: 409108-29-8
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: ZLIKXSJUWQYAIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  472.2±38.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  copper hydroxide 、 N-2-(3-phenylpropionyl)-α-amino-2-methylpropionic acid 以 水 、 异丙醇 为溶剂， 以64.02%的产率得到[Cu2(μ(2)-O2CC(CH3)2NHCOCH2CH2C6H5)4]
  参考文献：
  名称：

  Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide

  摘要：

  N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L-1)(TMAO)(2)] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L-1)(2-), coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L = 1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01291-8
• 作为产物：
  描述：

  2-(3-phenyl-propanoyl-amino)-isobutyric acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以97%的产率得到N-2-(3-phenylpropionyl)-α-amino-2-methylpropionic acid
  参考文献：
  名称：

  Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone

  摘要：

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.059

文献信息

• Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide
  作者：Wim Buijs、Peter Comba、Danny Corneli、Hans Pritzkow

  DOI：10.1016/s0022-328x(01)01291-8

  日期：2002.1

  N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L-1)(TMAO)(2)] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L-1)(2-), coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L = 1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction. (C) 2002 Elsevier Science B.V. All rights reserved.
• Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
  作者：Päivi H. Kiviranta、Heikki S. Salo、Jukka Leppänen、Valtteri M. Rinne、Sergiy Kyrylenko、Erkki Kuusisto、Tiina Suuronen、Antero Salminen、Antti Poso、Maija Lahtela-Kakkonen、Erik A.A. Wallén

  DOI：10.1016/j.bmc.2008.07.059

  日期：2008.9

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.