L-苯丙氨酸,4-硝基苯基酯,单氢溴化 | 14131-88-5

• 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: L-苯丙氨酸,4-硝基苯基酯,单氢溴化
• 英文名称: N-(S)-phenylalanine 4-nitrophenyl ester hydrobromide
• 英文别名: (4-nitrophenyl) (2S)-2-amino-3-phenylpropanoate;hydrobromide
• CAS: 14131-88-5
• 化学式: BrH*C₁₅H₁₄N₂O₄
• 分子量: 367.199
• InChiKey: LPSOZDDZZQCLLG-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 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：
  98.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸,4-硝基苯基酯,单氢溴化 在 potassium dihydrogenphosphate 、 sugar amide surfactant 、 lithium chloride 作用下， 以 水 、 乙腈 为溶剂， 生成 L-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-苄氧羰基-L-苯丙氨酸对硝基苯酯 在 氢溴酸 作用下， 生成 L-苯丙氨酸,4-硝基苯基酯,单氢溴化
  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

• Amino-acids and peptides. Part XXV. The mechanism of the base-catalysed racemisation of the p-nitrophenyl esters of acylpeptides
  作者：I. Antonovics、G. T. Young

  DOI：10.1039/j39670000595

  日期：——

  “direct exchange” mechanism of racemisation and that through the oxazolone, and it is concluded that such racemisation proceeds through the intermediate formation, racemisation, and coupling of the corresponding oxazolone. Evidence is also given that the conversion of benzyloxycarbonylglycyl-L-phenylalanine into its p-nitrophenyl ester by means of diphenyl-keten is accompanied by racemisation.

  的p苯甲酰基和苄氧羰基甘氨酰的硝基苯基酯大号-苯丙氨酸由三乙胺在二氯甲烷中速度远远超过是苄氧羰基和邻苯二甲酰基的类似酯外消旋大号-苯丙氨酸。结果表明，酰基肽酯与三乙胺可逆地反应，生成相应的恶唑酮，该平衡极大地有利于该酯。通过加入大量过量的苄氧羰基缩水甘油基苯丙氨酸衍生的恶唑酮，抑制了三乙胺对苯甲酰基缩水甘油基-L-苯丙氨酸对硝基苯酯的消旋作用，建议立即与p-硝基苯氧根阴离子，因此可防止形成外消旋酯的逆反应。该实验清楚地区分了外消旋的“直接交换”机理和通过恶唑酮的机理，得出的结论是，这种消旋通过相应的恶唑酮的中间体形成，消旋和偶联而进行。也有证据表明，通过二苯基-酮将苄氧羰基甘氨酰基-L-苯丙氨酸转化成其对硝基苯酯伴随着消旋作用。
• 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。
• Schnabel,E., Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 171 - 175
  作者：Schnabel,E.

  DOI：——

  日期：——
• 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：——