<1(R/S)-(N-CBZ-amino)-2-phenylethyl>methylphosphinic acid | 119012-13-4

• 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: <1(R/S)-(N-CBZ-amino)-2-phenylethyl>methylphosphinic acid
• 英文别名: 1-(ethoxycarbonylamino)-2-phenylethylmethylphosphinic acid；Methyl-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
• CAS: 119012-13-4
• 化学式: C₁₇H₂₀NO₄P
• 分子量: 333.324
• InChiKey: FAAFALMMECAALB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <1(R/S)-(N-CBZ-amino)-2-phenylethyl>methylphosphinic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以40 mg的产率得到(1-Amino-2-phenyl-ethyl)-methyl-phosphinic acid
  参考文献：
  名称：

  Antibody-Catalyzed Hydrolysis of an Unsubstituted Amide

  摘要：

  The generation of antibodies capable of catalyzing the unassisted hydrolysis of unactivated amides has been an enduring goal of research in the field. Antidialkylphosphinate 1 monoclonal antibodies were screened for their ability to catalyze the hydrolysis of four methyl esters and four primary amides at pH 5.0, 7.0, and 9.0. One of 68 antibodies, 13D11, enantiospecifically hydrolyzed the C-terminal carboxamide of a dansyl-alkylated derivative of (R)-phenylalaninamide (2b). At pH 9.0, 13D11 catalyzed amide hydrolysis with a k(cat) of 1.65 X 10(-7) s(-1) and a K-m of 432 mu M and was stereospecifically inhibited by hapten with a K-i of 14.0 mu M. A shorter, acetylated derivative 3b was not hydrolyzed by 13D11, demonstrating that dansyl-alkyl binding interactions are essential for catalysis. Equally active antibody preparations were obtained from two separate batches of ascites. The antibody Fab' fragment was prepared, purified, and found to retain full activity. Amidolytic activity was not abolished by any of nine inhibitors of natural proteolytic enzymes. The rate of uncatalyzed amide hydrolysis was experimentally determined to be 1.25 x 10(-9) s(-1), indicating an antibody catalytic rate enhancement (k(cat)/k(uncat)) of 132.

  DOI：

  10.1021/ja00094a003
• 作为产物：
  描述：

  (1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphinic acid methyl ester 在 lithium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 51.5h， 生成 <1(R/S)-(N-CBZ-amino)-2-phenylethyl>methylphosphinic acid
  参考文献：
  名称：

  Antibody-Catalyzed Hydrolysis of an Unsubstituted Amide

  摘要：

  The generation of antibodies capable of catalyzing the unassisted hydrolysis of unactivated amides has been an enduring goal of research in the field. Antidialkylphosphinate 1 monoclonal antibodies were screened for their ability to catalyze the hydrolysis of four methyl esters and four primary amides at pH 5.0, 7.0, and 9.0. One of 68 antibodies, 13D11, enantiospecifically hydrolyzed the C-terminal carboxamide of a dansyl-alkylated derivative of (R)-phenylalaninamide (2b). At pH 9.0, 13D11 catalyzed amide hydrolysis with a k(cat) of 1.65 X 10(-7) s(-1) and a K-m of 432 mu M and was stereospecifically inhibited by hapten with a K-i of 14.0 mu M. A shorter, acetylated derivative 3b was not hydrolyzed by 13D11, demonstrating that dansyl-alkyl binding interactions are essential for catalysis. Equally active antibody preparations were obtained from two separate batches of ascites. The antibody Fab' fragment was prepared, purified, and found to retain full activity. Amidolytic activity was not abolished by any of nine inhibitors of natural proteolytic enzymes. The rate of uncatalyzed amide hydrolysis was experimentally determined to be 1.25 x 10(-9) s(-1), indicating an antibody catalytic rate enhancement (k(cat)/k(uncat)) of 132.

  DOI：

  10.1021/ja00094a003

文献信息

• Acetals and N,N′-alkylidenebiscarbamates in the synthesis of N-protected α-aminophosphinic acids
  作者：M. E. Dmitriev、V. V. Ragulin

  DOI：10.1134/s107036321211028x

  日期：2012.11