2-<2-<4-phenyl>-1-hydroxyethyl>benzoic acid | 137998-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-<2-<4-phenyl>-1-hydroxyethyl>benzoic acid
• 英文别名: 2-[2-[4-[Bis(phenylmethyl)amino]phenyl]-1-hydroxyethyl]-benzoic acid；2-[2-[4-(dibenzylamino)phenyl]-1-hydroxyethyl]benzoic acid
• CAS: 137998-67-5
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: KJCLKWIUFPYSSL-UHFFFAOYSA-N

物化性质

• 沸点：
  652.0±55.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<2-<4-phenyl>-1-hydroxyethyl>benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到2-<2-(4-aminophenyl)-1-hydroxyethyl>benzoic acid
  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
• 作为产物：
  描述：

  4-硝基苯乙烯 在 palladium on activated charcoal lead(IV) acetate 、 盐酸 、 calcium sulfate 、 正丁基锂 、 Rexyn 101 (H) cation-exchange resin 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 63.0h， 生成 2-<2-<4-phenyl>-1-hydroxyethyl>benzoic acid
  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

• Molecules with antibody combining sites that catalyze hydrolysis
  申请人：Scripps Clinic and Research Foundation

  公开号：US05187086A1

  公开（公告）日：1993-02-16

  An antibody molecule or molecule containing antibody combining site portions (catalytic molecule) that catalytically hydrolyzes a preselected carboxylic acid amide or ester bond of a reactant ligand, methods of making and using the catalytic molecule, and cells that produce those molecules are disclosed. The catalytic molecules bind to a reactant ligand containing the bond to be hydrolyzed and also to a haptenic ligand. The haptenic ligand is structurally analogous to the reactant ligand and contains a tetrahedral carbon atom that is bonded to a hydroxyl group and to a saturated carbon atom at a position in the haptenic ligand that corresponds to position of the carbonyl group and its bonded heteroatom of the reactant ligand. The haptenic ligand also contains a group that bears an ionic charge in aqueous solution at physiological pH values that is not present at a corresponding position of the reactant ligand. The ionic charge-bearing group is located in the hapten within 7 .ANG.ngstroms of the tetrahedral carbon atom.

  本文介绍了一种抗体分子或含有抗体结合位点部分（催化分子），该催化分子具有催化水解反应配体的预选羧酸酰胺或酯键的能力，以及制备和使用该催化分子的方法和产生这些分子的细胞。催化分子结合到含有要水解的键的反应配体上，并且还结合到一个半抗原配体上。半抗原配体在结构上类似于反应配体，并且在半抗原配体中，一个四面体碳原子与一个羟基和一个饱和碳原子键合，该四面体碳原子的位置对应于反应配体的羰基团和其键合杂原子的位置。半抗原配体还包含一个在生理pH值下在水溶液中带有离子电荷的基团，该离子电荷基团在反应配体的相应位置上不存在。该带电基团在半抗原内距离四面体碳原子小于7埃。
• MOLECULES WITH ANTIBODY COMBINING SITES THAT CATALYSE HYDROLYSIS REACTIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP0512074B1

  公开（公告）日：1998-07-22
• 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：——
• US5187086A
  申请人：——

  公开号：US5187086A

  公开（公告）日：1993-02-16
• 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.