(S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester | 181213-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester
• CAS: 181213-26-3
• 化学式: C₃₄H₃₈N₄O₇S
• 分子量: 646.764
• InChiKey: OUGJIYZEKWSCBE-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  145.69
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 1,4-环己二烯 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.25h， 生成
  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：

  L-苯丙氨酸苄酯对甲苯磺酸盐 、 N-叔丁氧羰基-N(咪唑)-(4-甲基苯磺酰基)-L-组氨酸 在 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以65%的产率得到(S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl 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