4-[4-(4-Nitro-phenoxycarbonylmethyl)-phenylcarbamoyl]-butyric acid | 132369-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-[4-(4-Nitro-phenoxycarbonylmethyl)-phenylcarbamoyl]-butyric acid
• 英文别名: 5-[4-[2-(4-Nitrophenoxy)-2-oxoethyl]anilino]-5-oxopentanoic acid
• CAS: 132369-59-6
• 化学式: C₁₉H₁₈N₂O₇
• 分子量: 386.361
• InChiKey: ZOYCVFUHKDTRRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[4-(4-Nitro-phenoxycarbonylmethyl)-phenylcarbamoyl]-butyric acid 在 antibody NPN₄₃C₉ 、 ATC buffer 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-Carboxymethyl-phenylcarbamoyl)-butyric acid
  参考文献：
  名称：

  抗体催化的苯酯水解的替代作用：酰基抗体中间体的进一步证据

  摘要：

  已经研究了单克隆催化抗体 NPN43C9 对一系列对位取代苯基酯的水解。在 k cat /K m -pH 曲线中观察到的表观 pK a 从 8.9（对硝基苯酯）移至最大值 9.5（对甲基苯酯）。抗体催化的酯水解速率与 σ 参数的相关性提供 2.3 的 ρ 值，表明水解机制通过中性氮亲核试剂的攻击进行，与一般碱催化的低 ρ 值形成对比水解

  DOI：

  10.1021/ja00035a057
• 作为产物：
  描述：

  对硝基苯酚 、 4-(4-Carboxymethyl-phenylcarbamoyl)-butyric acid 在 C₁₈H₁₄N₃O₇P 、 H₅-67 antibody 作用下， 生成 4-[4-(4-Nitro-phenoxycarbonylmethyl)-phenylcarbamoyl]-butyric acid
  参考文献：
  名称：

  Catalytic Antibodies Generated via Homologous and Heterologous Immunization

  摘要：

  Two different immunization protocols using haptens 1 and 2 have been employed for the generation of catalytic antibodies capable of hydrolyzing ester 3. Three successive injections with one hapten 1 or 2, a protocol referred to as homologous immunization, provided hydrolytic antibodies with a rate acceleration in the range of 10(3)-10(4). These antibodies exhibited inhibitory activity only by the hapten used for the immunization. On the other hand, two successive injections with hapten 1 followed by a boost with hapten 2, a protocol referred to as heterologous immunization, induced catalytic antibodies with a rate acceleration up to 1.5 x 10(5). The majority of these catalytic antibodies possessed cross-reactivities to haptens 1 and 2, and the catalytic activities were effectively inhibited by both haptens. Control experiments have suggested that catalytic antibodies via heterologous immunization are derived through the unique stimulation of 1-primed memory B-cells by the secondary hapten 2, but not through the primary response of virgin B-cells by 2. Two catalytic antibodies H2-23 and H5H2-42, generated via homologous immunization with 2 and heterologous immunization with haptens 1 and 2, respectively, were selected for the detailed kinetic studies. Antibody H2-23 showed burst kinetic behavior and the burst phase was eliminated by the addition of p-nitrophenolate 5. Antibody H5H2-42 has no burst phase and exhibited high multiple turnover activity. The pH-dependent kinetic characterization of H5H2-42 suggested that bifunctional catalytic residues in the antibody combining site likely exist in the active site. These results imply that the heterologous immunization strategy offers a potential means of introducing multiple catalytic residues into antibody combining sites without recourse to complicated synthesis of multifunctional haptens.

  DOI：

  10.1021/ja00151a002

文献信息

• Suga; Ersoy; Williams, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 6025 - 6026
  作者：Suga、Ersoy、Williams、Tsumuraya、Margolies、Sinskey、Masamune

  DOI：——

  日期：——
• Jack Chen; Danon, Tami; Sastry, Lakshmi, Journal of the American Chemical Society, 1993, vol. 115, # 1, p. 357 - 358
  作者：Jack Chen、Danon, Tami、Sastry, Lakshmi、Mubaraki, Monica、Janda, Kim D.、Lerner, Richard A.

  DOI：——

  日期：——