D,L-phenylalanine p-nitrophenyl ester | 55895-89-1

• 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: D,L-phenylalanine p-nitrophenyl ester
• 英文别名: Phenylalanine p-nitrophenyl ester；phenylalanine-(4-nitro-phenyl ester)；Phenylalanin-(4-nitro-phenylester)；(4-Nitrophenyl) 2-amino-3-phenylpropanoate
• CAS: 55895-89-1
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: MHDRDPLGSXVGGV-UHFFFAOYSA-N

物化性质

• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D,L-phenylalanine p-nitrophenyl ester 在 溶剂黄146 、 亚硝酸异戊酯 作用下， 以 二氯甲烷 为溶剂， 生成 2-diazonio-1-(4-nitrophenoxy)-3-phenylprop-1-en-1-olate
  参考文献：
  名称：

  氨基酸和多肽—XIV：一种简便的制备α-取代的α-重氮酯的方法

  摘要：

  在少量有机酸存在的氯仿或苯中，用亚硝酸异戊酯处理16种α-氨基酸酯，然后在氧化铝上进行色谱纯化，得到相应的α-取代-α-重氮酯（1）。相当不错的产量。

  DOI：

  10.1016/0040-4020(75)85070-8
• 作为产物：
  描述：

  (4-nitrophenyl) 2-(decanoylamino)-3-phenylpropanoate 在 potassium chloride 、 双十二烷基二甲基溴化铵 、 Z-Phe-His-OH 作用下， 以 水 、 乙腈 为溶剂， 生成 D,L-phenylalanine p-nitrophenyl ester
  参考文献：
  名称：

  通过包括二肽型亲核试剂的双层囊泡系统对对硝基苯基N-酰基苯基丙氨酸的去酰化反应具有很高的立体选择性

  摘要：

  用包含二肽型亲核试剂和阳离子双链表面活性剂的双层囊泡体系对对硝基苯基N-酰基苯基丙氨酸进行脱酰基处理，可得到高立体选择性（25°C下k cat L / k cat D = 29.6和10°C下83.6）。的脱酰p硝基苯ñ -dodecanoylphenylalanate通过的催化系统ñ（ - ñ苄氧基羰基大号-leucyl） -大号-组氨酸和ñ，ñ -didodecyl- ñ，ñ -二甲基溴化物。

  DOI：

  10.1039/c39820000738

文献信息

• Retroviral protease inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0402646A1

  公开（公告）日：1990-12-19

  A retroviral protease inhibiting compound of the formula or a pharmaceutical acceptable salt, prodrug or ester thereof, wherein X is a linking group; A is (1) substituted amino, (2) substituted carbonyl, (3) functionalized imino, (4) functionalized alkyl, (5) functionalized acyl, (6) functionalized heterocyclic or (7) functionalized (heterocyclic)alkyl; and B is (1) substituted carbonyl independently defined as herein, (2) substituted amino independently defined as herein, (3) functionalized imino independently defined as herein, (4) functionalized alkyl independently defined as herein, (5) functionalized acyl independently defined as herein, (6) functionalized heterocyclic independently defined as herein or (7) functionalized (heterocyclic)alkyl independently defined as herein.

  式中的逆转录病毒蛋白酶抑制化合物 或其药物可接受的盐、原药或酯，其中 X 是连接基团； A 是 (1) 取代的氨基 (2) 取代的羰基 (3) 官能化亚氨基 (4) 官能化烷基 (5) 官能化酰基 (6) 官能化杂环或 (7) 官能化（杂环）烷基；且 B 是 (1) 如本文所独立定义的取代的羰基、 (2) 如本文所独立定义的取代氨基 (3) 如本文所独立定义的官能化亚氨基 (4) 如本文所独立定义的官能化烷基、 (5) 如本文所独立定义的官能化酰基、 (6) 如本文所独立定义的官能化杂环，或 (7) 本文独立定义的官能化（杂环）烷基。
• pH-indicator based assay for selective enzymes
  申请人：ThermoGen, Inc.

  公开号：US20020177180A1

  公开（公告）日：2002-11-28

  Provided herein is a method for the quantitative screening of hydrolase for desired substrate activity using pH indicators which are sensitive to the release of protons from a chemical reaction in a reaction mixture. The method comprises selecting buffer and indicator conditions such that both have the same affinity for protons such that the relative amount of buffer protonated is proportional to the amount of indicator protonated as the pH of the reaction mixture shifts. A reaction mixture is then prepared comprising a buffer, indicator, hydrolase to be tested, and desired substrate to be tested, allowing the hydrolase to react with the substrate. The reaction is monitored by detection of change in color of the reaction mixture, determined by the affect of the reaction on the indicator.

  本文提供了一种利用 pH 指示剂定量筛选水解酶所需底物活性的方法，pH 指示剂对反应混合物中化学反应释放的质子敏感。该方法包括选择缓冲液和指示剂条件，使两者对质子具有相同的亲和力，从而使缓冲液质子化的相对量与指示剂质子化的量成比例，随着反应混合物 pH 值的变化而变化。然后制备由缓冲液、指示剂、待测水解酶和所需底物组成的反应混合物，让水解酶与底物发生反应。通过检测反应混合物的颜色变化来监测反应，颜色变化由反应对指示剂的影响决定。
• Peptide Syntheses Via Amino Acid Active Esters¹
  作者：Murray Goodman、Kenneth C. Stueben

  DOI：10.1021/ja01524a040

  日期：1959.8
• Chiral Lipophilic Ligands. 1. Enantioselective Cleavage of .alpha.-Amino Acid Esters in Metallomicellar Aggregates
  作者：Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo00094a034

  日期：1994.7

  Several chiral ligands (1a,b, 2a-d), their marked lipophilic structure featuring a binding subunit comprising a 2-substituted pyridine, a tertiary amine, and a hydroxyl, have been synthesized and their complexes with Cu(II), Zn(II), or Co(II) ions investigated in homomicellar or comicellar aggregates as enantioselective catalysts of the cleavage of p-nitrophenyl esters of alpha-amino acids (Phe, Phg, Leu). Rate accelerations up to 3 orders of magnitude over the Cu(II) catalyzed hydrolysis and enantioselectivities ranging from; 3.2 to 11.6 have been observed. In each case explored, the chiral ligand reacts faster with the enantiomeric substrate of opposite absolute configuration. Several pieces of evidence indicate that the effective cleavage process in micellar aggregates involves the following: (a) the formation of a ternary (ligand-metal ion-substrate) complex; (b) within such a complex, a nucleophilic attack of the ligand hydroxyl on the substrate to give a transacylation intermediate; and (c) the metal ion promoted hydrolysis of the transacylation intermediate with a relatively fast turnover of the catalyst. Such a mode of action does not operate outside or in the absence of micellar aggregates: in this case; the hydroxyl is displaced by water that acts as the nucleophile ina slower (less enantioselective) process. The enantioselectivity of the transacylation process appears to be little affected by the steric interaction between the substituents at the chiral center of the amino acid ester and of the ligand. We suggest that the enantioselectivity arises from a different hydration, due to steric reasons, of the diastereomeric complexes comprising the two enantiomers of the substrate. As a consequence, the relevance of the competing mechanisms of cleavage of the ester, the first one, faster, involving the hydroxyl and the second one, slower, involving a Cu(II)-bound water molecule, may be different. In the case of the less hydrated, more hydrophobic R-S or S-R complex the former, faster, mode of cleavage may be more relevant than in the case of the more hydrated, less hydrophobic, S-S or R-R complex.
• Mechanism of enantioselective ester cleavage by histidine containing dipeptides at a micellar interface
  作者：Marco C. Cleij、Wiendelt Drenth、Roeland J. M. Nolte

  DOI：10.1021/jo00012a019

  日期：1991.6

  Chiral p-nitrophenyl esters derived from the amino acid phenylalanine are cleaved by histidine-containing dipeptides at a micellar interface. High enantioselectivities (up to k(L)/k(D) = 30.4 at 0-degrees-C) are observed. Both the substrates and the catalysts contain an alternating sequence of hydrophobic and hydrophilic groups. Due to the need for hydration of the hydrophilic groups, the hydrophobic groups cannot dissolve completely into the micellar hydrocarbon phase. The kinetic data suggest that the micellar interface is capable of discriminating between transition states that have different hydrophilic and hydrophobic properties. One of the diastereomeric transition states is characterized by a hydrogen bond between the amide CO group of the ester and an NH group of the histidine-containing dipeptide. Upon formation of this hydrogen bond these polar CO and NH groups lose their hydrophilicity which allows the transfer of the adjacent apolar groups to the micellar hydrocarbon phase. The other diastereomeric transition state cannot form this hydrogen bond and the hydrophobic groups remain hydrated. Consequently, the latter transition state is of higher energy. The kinetic data reveal that it is important to prevent steric hinderance between the reactants in order to allow the unhindered formation of the hydrogen bond.