(2S)-3-苯基-2-(苯基甲氧羰基氨基)丙酸(4-硝基苯基)酯 | 2578-86-1

• 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
• 中文名称: (2S)-3-苯基-2-(苯基甲氧羰基氨基)丙酸(4-硝基苯基)酯
• 英文名称: DL-N-(carbobenzoxy)phenylalanine p-nitrophenyl ester
• 英文别名: p-nitrophenyl ester of N-(benzyloxycarbonyl)-D,L-2-amino-3-phenylpropionic acid；p-nitrophenyl ester of N-benzyloxycarbonyl-D,L-phenylalanine；benzyloxycarbonyl-DL-phenylalanine p-nitrophenyl ester；(+/-)-N-Benzyloxycarbonyl-phenylalanin-(4-nitro-phenylester)；DL-N-(Benzyloxycarbonyl)-phenylalanin-p-nitrophenylester；Benzyloxycarbonyl-DL-phenylalanin-p-nitro-phenylester；(4-nitrophenyl) 3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 2578-86-1；95585-40-3
• 化学式: C₂₃H₂₀N₂O₆
• 分子量: 420.422
• InChiKey: TVENQUPLPBPLGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-3-苯基-2-(苯基甲氧羰基氨基)丙酸(4-硝基苯基)酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 22.5h， 生成 2-amino-N,N-dimethyl-3-phenylpropanamide
  参考文献：
  名称：

  Carbanions. Electron transfer vs. proton capture. 7. Electron-transfer oxidation of an amino acid derived carbanion

  摘要：

  DOI：

  10.1021/jo00316a004
• 作为产物：
  描述：

  对硝基苯酚 、 Cbz-DL-苯丙氨酸 在 吡啶 、 三氟乙酸苯酯 作用下， 生成 (2S)-3-苯基-2-(苯基甲氧羰基氨基)丙酸(4-硝基苯基)酯
  参考文献：
  名称：

  Rzeszotarska,B.; Vlasov,G.P., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1967, vol. 15, # 4, p. 143 - 147

  摘要：

  DOI：

文献信息

• STEREOSELECTIVE HYDROLYSIS OF AMINO ACID ESTERS BY MODIFIED POLY(ETHYLENIMINE)S WITH COVALENTLY-LINKED DIPEPTIDE CONTAINING A HISTIDYL RESIDUE
  作者：Yoshiharu Kimura、Mamoru Nango、Yasuji Ihara、Nobuhiko Kuroki

  DOI：10.1246/cl.1984.429

  日期：1984.3.5

  Stereoselective hydrolyses of chiral substrates were examined in poly(ethylenimine) derivatives with optically active groups. A high stereoselective effect, kL/kD=3.6, is observed. The effect of the substrate structure influenced both the rate constant and the stereoselective ratio in the hydrolyses by poly(ethylenimine) derivatives.

  在具有光学活性基团的聚（乙烯亚胺）衍生物中检查手性底物的立体选择性水解。观察到高立体选择性效应，kL/kD=3.6。底物结构的影响影响了聚（乙烯亚胺）衍生物水解的速率常数和立体选择性比。
• Synthesis of peptide oxazolones and related compounds
  作者：W.J. McGahren、M. Goodman

  DOI：10.1016/0040-4020(67)80036-x

  日期：1967.5

  2-(1′-benzyloxycarbonylamino-1′-methyl)ethyl-4-methyl-oxazolone and 2-(1′-benzyloxycarbonylamino-1′-methyl)ethyl-4-benzyloxazolone, were prepared and characterized. the imidazole-acceleratedp-nitrophenyl-active ester synthesis was found to be a good route to the dipeptides benzyloxycarbonylaminoisobutyryl-l-phenylalanine methyl ester and benzyloxycarbonylaminoisobutyryl-l-alanine methyl ester. The acids were

  两个光学活性的晶体肽恶唑酮是2-（1'-苄氧基羰基氨基-1'-甲基）乙基-4-甲基-恶唑酮和2-（1'-苄氧基羰基氨基-1'-甲基）乙基-4-苄基恶唑酮。准备和表征。发现咪唑促进的对硝基苯基活性酯的合成是获得二肽苄氧基羰基氨基异丁酰基-1-苯丙氨酸甲酯和苄氧基羰基氨基异丁酰基-1-丙氨酸甲酯的良好途径。通过用稀酸小心水解这些酯并闭环，与乙酸酐或二环己基-碳二亚胺反应生成恶唑酮，从而得到酸。
• MOLECULARLY IMPRINTED POLYMERS, METHODS FOR THEIR PRODUCTION AND USES THEREOF
  申请人：Hearn Milton T.W.

  公开号：US20120225962A1

  公开（公告）日：2012-09-06

  The present invention relates to methods of preparing molecularly imprinted polymers (MIPs) which facilitate chemical hydrolysis and more particularly the hydrolysis of chemical substrates which possess hydrolytically labile bonds such as peptides and proteins. The present invention is thus directed to MIPs designed to possess hydrolytic activity, methods for preparing such MIPs and uses of the MIPs.

  本发明涉及制备分子印迹聚合物（MIPs）的方法，该方法促进化学水解，更具体地，促进具有水解敏感键的化学底物（例如肽和蛋白质）的水解。因此，本发明针对设计具有水解活性的MIPs，制备这种MIPs的方法以及MIPs的用途。
• 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.