(2S)-2-[双(羧甲基)氨基]-3-甲基丁酸 | 936356-83-1

• 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-甲基丁酸
• 英文名称: S-BCMVA(2H)
• 英文别名: N,N-bis(carboxymethyl(+H))-S-valine；N,N-Bis(carboxymethyl)-L-valine；(2S)-2-[bis(carboxymethyl)amino]-3-methylbutanoic acid
• CAS: 936356-83-1
• 化学式: C₉H₁₅NO₆
• 分子量: 233.221
• InChiKey: MNKCOPCEKKDGGV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2S)-2-[双(羧甲基)氨基]-3-甲基丁酸 、 [(RuCl2(2,2'-bipyridine))2Cl2]*0.5H2O 、 potassium chloride 在 Et₃N 作用下， 以 乙醇 为溶剂， 生成 K[Ru(bpy)(S-BCMVA)]
  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

文献信息

• 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
  作者：Takashi Kato、Hideyuki Kumita、Isao Takahashi、Aki Murakami、Kunue Yoshimoto、Yasunori Ikeue、Kunishige Kataoka、Shinnichiro Suzuki、Takeshi Sakurai、Tomohiro Ozawa、Koichiro Jitsukawa、Hideki Masuda

  DOI：10.1016/j.ica.2006.08.033

  日期：2007.4

  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.