D-1-aminoethylphosphonous acid | 71937-29-6

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: D-1-aminoethylphosphonous acid
• 英文别名: (1S)-1-aminoethylphosphinic acid；[(1S)-1-aminoethyl]phosphinic acid
• CAS: 71937-29-6
• 化学式: C₂H₈NO₂P
• 分子量: 109.065
• InChiKey: TVKUNRSARHGLNB-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 D-1-aminoethylphosphonous acid 生成 ((S)-1-tert-Butoxycarbonylamino-ethyl)-phosphinic acid
  参考文献：
  名称：

  Antibody-catalyzed cleavage of the d -Ala- d -Lac depsipeptide: An immunological approach to the problem of vancomycin resistance

  摘要：

  Vancomyein resistance is currently a major healthcare problem. The development of a catalytic monoclonal antibody (mAb) that hydrolyzes the D-Ala-D-Lac depsipeptide provides a potentially novel antibiotic strategy. A phosphonate hapten design was used to program antibody catalysis. The characteristics of the hapten were shown to be important for obtaining a viable immune response and several catalytic mAbs that cleave a peptidoglycan model substrate. The best mAb afforded a > 500-fold rate enhancement over background. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00047-1
• 作为产物：
  描述：

  N-benzyloxycarbonyl-1(S)-aminoethylphosphonic acid 在 氢溴酸 作用下， 生成 D-1-aminoethylphosphonous acid
  参考文献：
  名称：

  Antibody-catalyzed cleavage of the d -Ala- d -Lac depsipeptide: An immunological approach to the problem of vancomycin resistance

  摘要：

  Vancomyein resistance is currently a major healthcare problem. The development of a catalytic monoclonal antibody (mAb) that hydrolyzes the D-Ala-D-Lac depsipeptide provides a potentially novel antibiotic strategy. A phosphonate hapten design was used to program antibody catalysis. The characteristics of the hapten were shown to be important for obtaining a viable immune response and several catalytic mAbs that cleave a peptidoglycan model substrate. The best mAb afforded a > 500-fold rate enhancement over background. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00047-1

文献信息

• McCleery, Patrick P.; Tuck, Brian, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1319 - 1329
  作者：McCleery, Patrick P.、Tuck, Brian

  DOI：——

  日期：——
• Enzymatic preparation of both L- and D-enantiomers of phosphonic and phosphonous analogues of alanine using penicillin acylase
  作者：Vladimir A. Solodenko、Michail Y. Belik、Sergei V. Galushko、Valeri P. Kukhar、Elena V. Kozlova、Dmitri A. Mironenko、Vitas K. Svedas

  DOI：10.1016/s0957-4166(00)82240-5

  日期：1993.1

  D-Enantiomers of N-acylated 1-aminoethylphosphonic and 1-aminoethylphosphonous acids were able to be hydrolyzed with high concentrations of penicillin acylase in a reasonable time period. This finding was used to prepare both L- and D-enantiomers of these phosphorus analogues of alanine by stepwise enzymatic hydrolysis of their racemic N-phenylacetyl derivatives using the same enzyme - penicillin acylase - by simply changing the enzyme/substrate ratio.
• Antibody-catalyzed cleavage of the d -Ala- d -Lac depsipeptide: An immunological approach to the problem of vancomycin resistance
  作者：Shigeki Isomura、Jon A Ashley、Peter Wirsching、Kim D Janda

  DOI：10.1016/s0960-894x(02)00047-1

  日期：2002.3

  Vancomyein resistance is currently a major healthcare problem. The development of a catalytic monoclonal antibody (mAb) that hydrolyzes the D-Ala-D-Lac depsipeptide provides a potentially novel antibiotic strategy. A phosphonate hapten design was used to program antibody catalysis. The characteristics of the hapten were shown to be important for obtaining a viable immune response and several catalytic mAbs that cleave a peptidoglycan model substrate. The best mAb afforded a > 500-fold rate enhancement over background. (C) 2002 Published by Elsevier Science Ltd.