(4S)-4-acetamido-5-(4-nitroanilino)-5-oxopentanoic acid | 41149-11-5

• 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
• 英文名称: (4S)-4-acetamido-5-(4-nitroanilino)-5-oxopentanoic acid
• CAS: 41149-11-5
• 化学式: C₁₃H₁₅N₃O₆
• 分子量: 309.279
• InChiKey: SDTVKGSMFQVLAM-NSHDSACASA-N

物化性质

• 沸点：
  716.4±60.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-4-acetamido-5-(4-nitroanilino)-5-oxopentanoic acid 在 glutamyl endopeptidase from Alcalase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 4-硝基苯胺
  参考文献：
  名称：

  Substrate specificity of glutamyl endopeptidase (GE): Hydrolysis studies with a bovine α-casein preparation

  摘要：

  Glutamyl endopeptidase (GE) from Alcalase (TM) 2.4 L was purified using hydrophobic interaction (HIC) and ion-exchange (IEX) chromatography. The yield of GE obtained was approximately 42%. Bovine alpha-casein (containing alpha(s1)- and alpha(s2)-casein) was digested with GE at 37 and 50 degrees C for 4 h. Samples were withdrawn at various time intervals and the peptides generated were analysed using mass spectrometry. GE activity was highly specific and hydrolysed the peptide bond predominantly on the carboxy side of Glu residues while hydrolysis on the carboxyl side of Asp residues was also observed. Hydrolysis did not occur when Pro was at the P-1' position. In Glu-Glu-X (X = Arg, Asn, Ile and Ser) and Glu-Glu-Glu-Lys sequences, hydrolysis of Glu-X and Glu-Lys was preferred. The results are relevant to our understanding of the hydrolytic specificity of Alcalase, a food-grade proteolytic preparation containing GE activity which is used in the generation of casein hydrolysates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.08.038
• 作为产物：
  描述：

  乙酸酐 、 4-硝基苯胺 、 N-芴甲氧羰基-L-谷氨酸 1-烯丙基酯 以80%的产率得到(4S)-4-acetamido-5-(4-nitroanilino)-5-oxopentanoic acid
  参考文献：
  名称：

  N-[Chloro(dimethylamino)methylene]-N-methylmethanaminium chloride (TMUCl Cl), the reagent of choice for the solid-phase synthesis of anilides

  摘要：

  An effective solid-phase preparation of anilides from supported carboxylic acids is described by their activation as the corresponding acid chlorides with TMUCI Cl. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.140

文献信息

• N-[Chloro(dimethylamino)methylene]-N-methylmethanaminium chloride (TMUCl Cl), the reagent of choice for the solid-phase synthesis of anilides
  作者：Marc Vendrell、Rubén Ventura、Ariel Ewenson、Miriam Royo、Fernando Albericio

  DOI：10.1016/j.tetlet.2005.05.140

  日期：2005.8

  An effective solid-phase preparation of anilides from supported carboxylic acids is described by their activation as the corresponding acid chlorides with TMUCI Cl. (c) 2005 Elsevier Ltd. All rights reserved.
• Substrate specificity of glutamyl endopeptidase (GE): Hydrolysis studies with a bovine α-casein preparation
  作者：Phanindra Kalyankar、Yishen Zhu、Martina O’ Keeffe、Gerard O’ Cuinn、Richard J. FitzGerald

  DOI：10.1016/j.foodchem.2012.08.038

  日期：2013.1

  Glutamyl endopeptidase (GE) from Alcalase (TM) 2.4 L was purified using hydrophobic interaction (HIC) and ion-exchange (IEX) chromatography. The yield of GE obtained was approximately 42%. Bovine alpha-casein (containing alpha(s1)- and alpha(s2)-casein) was digested with GE at 37 and 50 degrees C for 4 h. Samples were withdrawn at various time intervals and the peptides generated were analysed using mass spectrometry. GE activity was highly specific and hydrolysed the peptide bond predominantly on the carboxy side of Glu residues while hydrolysis on the carboxyl side of Asp residues was also observed. Hydrolysis did not occur when Pro was at the P-1' position. In Glu-Glu-X (X = Arg, Asn, Ile and Ser) and Glu-Glu-Glu-Lys sequences, hydrolysis of Glu-X and Glu-Lys was preferred. The results are relevant to our understanding of the hydrolytic specificity of Alcalase, a food-grade proteolytic preparation containing GE activity which is used in the generation of casein hydrolysates. (c) 2012 Elsevier Ltd. All rights reserved.