(2S)-2-[双(羧甲基)氨基]-3-苯基丙酸 | 6710-91-4

• 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: (2S)-2-[双(羧甲基)氨基]-3-苯基丙酸
• 英文名称: bis-N,N-carboxymethyl-(S)-phenylalanine
• 英文别名: N,N-bis-carboxymethyl-L-phenylalanine；N,N-bis(carboxymethyl(H))-S-phenylalanine；S-BCMPA(2H)；N,N-Bis-carboxymethyl-L-phenylalanin；N,N-Bis(carboxymethyl)-L-phenylalanine；(2S)-2-[bis(carboxymethyl)amino]-3-phenylpropanoic acid
• CAS: 6710-91-4
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: HWXFTWCFFAXRMQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(RuCl2(2,2'-bipyridine))2Cl2]*0.5H2O 、 (2S)-2-[双(羧甲基)氨基]-3-苯基丙酸 、 potassium chloride 在 Et₃N 作用下， 以 乙醇 为溶剂， 生成 K[Ru(bpy)(S-BCMPA)]
  参考文献：
  名称：

  Probing electron transfer reactions between two azurins from Alcaligenes xylosoxidans GIFU 1051 with optically active Ru complexes as molecular recognition probes: Importance of the 43rd residue

  摘要：

  Electron transfer reactions between optically-active Ru-II/III complexes incorporating (S)-/(R)-amino acids, and the two azurins, azurin-1 (az-1Cu) and azurin-2 (az-2Cu) isolated from Alcaligenes xylosoxidans GIFU 1051, have been studied to probe molecular recognition sites on the two azurins. The Ru-II/III complexes are K[Ru-II(L)(bpy)] and [Ru-III(L)(bpy)], and have a tripodal ligand (L) derived from the (S)-/(R)-amino acids, which are in turn exchanged for other functional substituent groups, such as (S)-/(R)-phenylaianine, -leucine, -valine, -alanine, and -glutamic acid (L = (S)-/(R)-BCMPA, -BCMLE, -BCMVA, -BCMAL, and -BCMGA). In the oxidation reaction of az-1Cu(1) promoted by the Ru-III complexes, the kinetic parameters exhibited enantio- and stereo-selectivities, while the same reaction of az-2Cu(1) was less enantio- and stereo-selective. These differences suggest that the processes of formation of the activated states are different for the two azurins. On the other hand, such a difference has not been observed for az-1 and az-2 with respect to the reduction reactions promoted by both azurins Cull by the Ru-II complexes within the experimental error. This suggests that the neutrality of the Ru complexes is important for precise molecular recognition of azurins. His 117 has been proposed as the electron transfer site. The local structures in the vicinity of the His 117 side chain in the two azurins, are essentially identical with the exception of the 43rd residue, Va143 and Ala43 for az-1 and az-2, respectively. Electron transfer reactions between Ru-III complexes and a mutant azurin, V43A-az-1, were also carried out. Interestingly, the activation parameters estimated were very similar to those of az-2, indicating that the 43rd residue acts as the electron transfer site in azurins and provides rationalization for the different mechanisms of az-1 and az-2 in redox reactions. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2006.08.033
• 作为产物：
  描述：

  L-苯丙氨酸 在 magnesium bromoacetate 、 水 、 magnesium oxide 作用下， 生成 N-carboxymethyl-L-phenylalanine 、 (2S)-2-[双(羧甲基)氨基]-3-苯基丙酸
  参考文献：
  名称：

  Korman; Clarke, Journal of Biological Chemistry, 1956, vol. 221, p. 113,116

  摘要：

  DOI：

文献信息

• Site-Selective Recognition of Amino Acids by Co(III) Complexes Containing a (N)(O)₃-Type Tripodal Tetradentate Ligand
  作者：Hideyuki Kumita、Taiju Morioka、Tomohiro Ozawa、Koichiro Jitsukawa、Hisahiko Einaga、Hideki Masuda

  DOI：10.1246/bcsj.74.1035

  日期：2001.6

  [Co(bcmpa)(aa)] complex in the trans(N)-configuration mode, rather than in the cis(N)-form. By using amino acid derivatives with bulky substituents at their amino or carboxylate sites under a neutral condition, the reactions have been demonstrated to be initiated by coordination of the amino nitrogen site. Interestingly, the cis(N)-complex, which is isolated as a minor product, isomerizes to the trans(N)-form

  双-N,N-羧甲基-(S)-苯丙氨酸碳合钴(III)复合物，[Co(bcmpa)(CO3)]2−，已被制备为一个简单的模型，能够识别氨基酸（Haa ) 其在溶液中的配位行为已通过电子吸收 (AB)、圆二色性 (CD) 和 1H NMR 光谱表征。K2[Co(bcmpa)( )] 复合物与氨基酸 (Haa) 的反应主要以反式 (N) 构型模式提供 [Co(bcmpa)(aa)] 复合物，而不是顺式(N)-形式。通过在中性条件下使用在其氨基或羧酸盐位点具有大取代基的氨基酸衍生物，已证明反应是由氨基氮位点的配位引发的。有趣的是，作为次要产物分离的顺式（N）复合物，在 pH 7 的水溶液中，在活性炭存在下异构化为反式 (N)-形式。Haa 与 [Co(bcmpa)( )]2− 复合物的位点选择性配位和立体选择性异构体...
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