5-{[4-(苯甲酰基氨基)苯基]氨基}-5-氧代戊酸 | 134485-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-{[4-(苯甲酰基氨基)苯基]氨基}-5-氧代戊酸
• 英文名称: 5-<<4-(benzoylamino)phenyl>amino>-5-oxopentanoic acid
• 英文别名: 5-(4-Benzamidoanilino)-5-oxopentanoic acid
• CAS: 134485-49-7
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: JRPKKIZMGDELLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  戊二酸酐 、 4-氨基苯甲酰苯胺 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到5-{[4-(苯甲酰基氨基)苯基]氨基}-5-氧代戊酸
  参考文献：
  名称：

  Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties

  摘要：

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.

  DOI：

  10.1021/ja00014a039

文献信息

• JANDA, KIM D.;WEINHOUSE, MICHAEL I.;DANON, TAMI;PACELLI, KAREN A.;SCHLOED+, J. AMER. CHEM. SOC., 113,(1991) N4, C. 5427-5434
  作者：JANDA, KIM D.、WEINHOUSE, MICHAEL I.、DANON, TAMI、PACELLI, KAREN A.、SCHLOED+

  DOI：——

  日期：——
• Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties
  作者：Kim D. Janda、Michael I. Weinhouse、Tami Danon、Karen A. Pacelli、Diane M. Schloeder

  DOI：10.1021/ja00014a039

  日期：1991.7

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.