(4-nitrophenyl) (2R)-2-amino-3-phenylpropanoate;hydrobromide | 69555-88-0

• 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: (4-nitrophenyl) (2R)-2-amino-3-phenylpropanoate;hydrobromide
• CAS: 69555-88-0
• 化学式: BrH*C₁₅H₁₄N₂O₄
• 分子量: 367.199
• InChiKey: LPSOZDDZZQCLLG-PFEQFJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.64
• 重原子数：
  22
• 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：
  99.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl) (2R)-2-amino-3-phenylpropanoate;hydrobromide 在 potassium dihydrogenphosphate 、 sugar amide surfactant 、 lithium chloride 作用下， 以 水 、 乙腈 为溶剂， 生成 D-phenylalanine hydrobromide
  参考文献：
  名称：

  Enantioselective hydrolysis of an α-amino acid ester in sugar-derived surfactant micelles

  摘要：

  p-Nitrophenyl ester of D-phenylalanine hydrogen bromide was hydrolyzed much faster than that of the corresponding L-isomer in the micelles formed with sugar-derived surfactants such as N-dodecylmaltobionamide. The enantioselectivity was largely affected by the alkyl chain length as well as the structure of the sugar part of the surfactant. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00767-9
• 作为产物：
  描述：

  N-[(苯基甲氧基)羰基]-D-苯丙氨酸 4-硝基苯基酯 在 氢溴酸 作用下， 生成 (4-nitrophenyl) (2R)-2-amino-3-phenylpropanoate;hydrobromide
  参考文献：
  名称：

  Hybrid Liposomes Coupled to Steric Control with High Enantioselectivity

  摘要：

  With respect to the hydrolysis of enantiomeric substrates (p-nitrophenyl N-dodecanoyl-D(L)phenylalaninate; C-12-D(L)-Phe-PNP) by the tripeptide catalyst (N-(benzyloxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine; Z-PheHisLeu), a remarkably high enantioselectivity (k(a/obsd)(L)/k(a/obsd)(D) = 28) along with marked rate-enhancement of the hydrolytic cleavage of C-12-D(L)-Phe-PNP was obtained with specific coaggregates of 32 mol % L-alpha-dipalmitoylphosphatidylcholine (DPPC) and 68 mol % alpha[4-(1,1,3,3-tetramethylbutyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl)(TritonX-100). Tile enantioselectivity was maximized at the phase transition temperature (T-e) in the 65 mol % DPPC/35 mol % TrixonX-100 and 32 mol % DPPC/68 mol % TritonX-100 coaggregate systems. The hydrophobicity and fluidity of the coaggregates can apparently be changed around T-e on tile basis of isokinetic temperature and fluorescence parameter studies.

  DOI：

  10.1021/jo00116a016

文献信息

• Novel bicyclic chiral crown ethers having a p-xylenedioxy unit with improved complex stability and rate-enhancement in the intra-complex thiolysis of .ALPHA.-amino acid ester salts.
  作者：Tatsuro YASUKATA、Shigeki SASAKI、Kenji KOGA

  DOI：10.1248/cpb.39.530

  日期：——

  Novel bicyclic chiral crown ethers having an α, α'-p-xylenedioxy unit were synthesized. Crown dithiol 1 with a p-xylenedioxy bridge-structure perfomed intra-complex thiolysis with α-amino acid p-nitrophenyl ester HBr salts much faster than the corresponding dithiol 3 without the bridge-structure. A 1H-NMR study suggested that the increased rate of intracomplex thiolysis is due to increased stability of the intermediary complex during the reaction.

  合成了具有 α, α'-p-xylenedioxy 单元的新型双环手性冠醚。具有对二亚甲氧基桥结构的冠醚 1 与α-氨基酸对硝基苯酯 HBr 盐进行络合物内硫解的速度比相应的无桥结构的二硫醇 3 快得多。1H-NMR 研究表明，络合物内硫解速度的提高是由于中间络合物在反应过程中稳定性的提高。
• Fairly Marked Enantioselectivity for the Hydrolysis of Amino Acid Esters by Chemically Modified Enzymes¹
  作者：Yoshihiro Yano、Kenji Shimada、Jiro Okai、Koichi Goto、Yoko Matsumoto、Ryuichi Ueoka

  DOI：10.1021/jo0265075

  日期：2003.2.1

  The hydrolysis (deacylation) of enantiomeric substrates by the chemically modified enzymes decanoyl-alpha-chymotrypsin and decanoyl-trypsin was studied. Reaction activity for decanoyl-alpha-chymotrypsin was lower than that for the native enzyme, although intriguingly the enantioselectivity was markedly enhanced as compared with the native enzyme. In particular, the apparently complete enantioselective

  研究了化学修饰的癸酰基-α-胰凝乳蛋白酶和癸酰基-胰蛋白酶对映体底物的水解（脱酰作用）。癸酰基-α-胰凝乳蛋白酶的反应活性低于天然酶，尽管有趣的是，与天然酶相比，对映选择性显着提高。特别地，对于对硝基苯基N-十二烷酰基-D（L）-苯丙氨酸酯的水解裂解，获得了显然完全的对映选择性催化。然而，癸酰基胰蛋白酶未观察到对映选择性的增强。这些结果表明通过添加疏水基团的化学修饰的α-胰凝乳蛋白酶已经促进了对疏水酯水解的对映选择性。
• Sasaki, Shigeki; Kawasaki, Motoji; Koga, Kenji, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 10, p. 4247 - 4266
  作者：Sasaki, Shigeki、Kawasaki, Motoji、Koga, Kenji

  DOI：——

  日期：——
• Enantioselective hydrolysis of an α-amino acid ester in sugar-derived surfactant micelles
  作者：Toshiyuki Kida、Kazuhiko Isogawa、Wanbin Zhang、Yohji Nakatsuji、Isao Ikeda

  DOI：10.1016/s0040-4039(98)00767-9

  日期：1998.6

  p-Nitrophenyl ester of D-phenylalanine hydrogen bromide was hydrolyzed much faster than that of the corresponding L-isomer in the micelles formed with sugar-derived surfactants such as N-dodecylmaltobionamide. The enantioselectivity was largely affected by the alkyl chain length as well as the structure of the sugar part of the surfactant. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Hybrid Liposomes Coupled to Steric Control with High Enantioselectivity
  作者：Koichi Goto、Yoko Matsumoto、Ryuichi Ueoka

  DOI：10.1021/jo00116a016

  日期：1995.6

  With respect to the hydrolysis of enantiomeric substrates (p-nitrophenyl N-dodecanoyl-D(L)phenylalaninate; C-12-D(L)-Phe-PNP) by the tripeptide catalyst (N-(benzyloxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine; Z-PheHisLeu), a remarkably high enantioselectivity (k(a/obsd)(L)/k(a/obsd)(D) = 28) along with marked rate-enhancement of the hydrolytic cleavage of C-12-D(L)-Phe-PNP was obtained with specific coaggregates of 32 mol % L-alpha-dipalmitoylphosphatidylcholine (DPPC) and 68 mol % alpha[4-(1,1,3,3-tetramethylbutyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl)(TritonX-100). Tile enantioselectivity was maximized at the phase transition temperature (T-e) in the 65 mol % DPPC/35 mol % TrixonX-100 and 32 mol % DPPC/68 mol % TritonX-100 coaggregate systems. The hydrophobicity and fluidity of the coaggregates can apparently be changed around T-e on tile basis of isokinetic temperature and fluorescence parameter studies.