(S)-2-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoyloxy]-3-phenyl-propionic acid methyl ester | 181213-17-2

• 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: (S)-2-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoyloxy]-3-phenyl-propionic acid methyl ester
• CAS: 181213-17-2
• 化学式: C₂₆H₂₈NO₇P
• 分子量: 497.485
• InChiKey: YRMRYBAYWRELIC-BJKOFHAPSA-N

反应信息

• 作为反应物：
  描述：

  (S)-2-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoyloxy]-3-phenyl-propionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-{(R)-1-[Hydroxy-((S)-1-methoxycarbonyl-2-phenyl-ethoxy)-phosphoryl]-2-phenyl-ethylcarbamoyl}-butyric acid; compound with triethyl-amine
  参考文献：
  名称：

  Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity

  摘要：

  A series of five haptens have been synthesized for use in in vitro selection experiments from combinatorial antibody libraries. Haptens were designed for the recruitment of serine and cysteine protease reaction mechanisms for the cleavage of Phe-Ala and Phe-Phe (L,L) dipeptide analogues. For the selection of transition state stabilization, Phe(P)(O)Ala (7) and PheP(O)Phe (10) derivatives were synthesized using the Mitsunobu approach where Phe(P) represents the phosphonic acid analogue of phenylalanine and (O)Phe and (O)Ala represent (L)-beta-phenyllactic and (L)-lactic acid, respectively. Optically pure peptidyl diazomethyl ketones 16 and 22 were synthesized for selection of the catalytic ensemble of cysteine proteases. An optically pure dipeptidyl boronic acid 26 was synthesized for the selection of the catalytic ensemble of serine proteases. A strategy for the evolution of catalytic antibodies using these haptens was developed which includes mechanism-based selections. Since mechanism based selections result in covalent trapping of species from libraries, diol and disulfide containing haptenic linkers were developed for the oxidative or reductive release of selected catalysts. Copyright 1O 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00085-5
• 作为产物：
  描述：

  在 三甲基溴硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (S)-2-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoyloxy]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity

  摘要：

  A series of five haptens have been synthesized for use in in vitro selection experiments from combinatorial antibody libraries. Haptens were designed for the recruitment of serine and cysteine protease reaction mechanisms for the cleavage of Phe-Ala and Phe-Phe (L,L) dipeptide analogues. For the selection of transition state stabilization, Phe(P)(O)Ala (7) and PheP(O)Phe (10) derivatives were synthesized using the Mitsunobu approach where Phe(P) represents the phosphonic acid analogue of phenylalanine and (O)Phe and (O)Ala represent (L)-beta-phenyllactic and (L)-lactic acid, respectively. Optically pure peptidyl diazomethyl ketones 16 and 22 were synthesized for selection of the catalytic ensemble of cysteine proteases. An optically pure dipeptidyl boronic acid 26 was synthesized for the selection of the catalytic ensemble of serine proteases. A strategy for the evolution of catalytic antibodies using these haptens was developed which includes mechanism-based selections. Since mechanism based selections result in covalent trapping of species from libraries, diol and disulfide containing haptenic linkers were developed for the oxidative or reductive release of selected catalysts. Copyright 1O 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00085-5