4-(4-Carboxymethyl-phenylcarbamoyl)-butyric acid | 122054-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-Carboxymethyl-phenylcarbamoyl)-butyric acid
• 英文别名: 4-{[4-(Carboxymethyl)phenyl]carbamoyl}butanoic acid；5-[4-(carboxymethyl)anilino]-5-oxopentanoic acid
• CAS: 122054-84-6
• 化学式: C₁₃H₁₅NO₅
• mdl: MFCD01923004
• 分子量: 265.266
• InChiKey: KCQGYPGOPDEMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-[4-(3-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

文献信息

• Substrate attenuation: An approach to improve antibody catalysis
  作者：Kim D. Janda、Stephen J. Benkovic、Donald A. McLeod、Diane M. Schloeder、Richard A. Lerner

  DOI：10.1016/s0040-4020(01)81784-1

  日期：1991.1

  Antibodies raised to quinaldine phosphonamide 1a showed no ability to hydrolyze its most homologous substrates amide and ester 2 and 3, respectively. However, within this same set of antibodies some thirteen showed a great propensity to hydrolyse a structurally similar naphthyl ester In addition to heteroatom discrimination one of the antibodies examined in detail displayed an increase in catalytic efficiency presumably via weak apparent binding (k(m)) when phenylesters were employed as substrates. These findings suggest abzyme catalysis may be improved via substrate attenuation.
• A Simple Protocol for the Modular Assembly of“Millipede” Artificial Enzymes
  作者：William B. Motherwell、Catherine E. Atkinson、Abil E. Aliev、Stephanie Y. F. Wong、Brian H. Warrington

  DOI：10.1002/anie.200352370

  日期：2004.2.27
• Immobilized catalytic antibodies in aqueous and organic solvents
  作者：Kim D. Janda、Jon A. Ashley、Teresa M. Jones、Donald A. McLeod、Diane M. Schloeder、Michael I. Weinhouse

  DOI：10.1021/ja00180a035

  日期：1990.11
• 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：——
• Substituent effects of an antibody-catalyzed hydrolysis of phenyl esters: further evidence for an acyl-antibody intermediate
  作者：Richard A. Gibbs、Patricia A. Benkovic、Kim D. Janda、Richard A. Lerner、Stephen J. Benkovic

  DOI：10.1021/ja00035a057

  日期：1992.4

  The hydrolysis of a series of para-substituted phenyl esters by the monoclonal catalytic antibody NPN43C9 has been investigated. The apparent pK a observed in the k cat /K m -pH profiles shifts from 8.9 (p-nitrophenyl ester) up to a maximum of 9.5 (p-methylphenyl ester). A correlation of the antibody-catalyzed rates of hydrolysis of the esters versus the σ parameter affords a ρ value of 2.3, indicative

  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