ethyl 2-(2-amino-4-methylpentanamido)propanoate | 58455-27-9

• 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: ethyl 2-(2-amino-4-methylpentanamido)propanoate
• 英文别名: Leu-Ala-OC2H5；Leu-Ala-OEt；ethyl (2S)-2-[(2S)-2-amino-4-methylpentanamido]propanoate；ethyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]propanoate
• CAS: 58455-27-9
• 化学式: C₁₁H₂₂N₂O₃
• 分子量: 230.307
• InChiKey: BSPYGNIRRUZXCI-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-amino-4-methylpentanamido)propanoate 在 哌啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.66h， 生成 Ph-NHCO-Ser(OtBu)-Leu-Ala-OEt
  参考文献：
  名称：

  Structural Modification of Fas C-Terminal Tripeptide and Its Effects on the Inhibitory Activity of Fas/FAP-1 Binding

  摘要：

  We report the structural requirements of the C-terminal tripeptide derivative of Fas (Ac-Ser-Leu-Val-OH, 1) for the inhibitory activity of Fas/FAP-1 binding. The presence of a carboxyl group and a L-Val residue at the C-terminus is essential for the inhibitory activity, and the hydroxyl group of Ser plays an important role as the donor of a hydrogen bond. The introduction of hydrophobic groups to the N-terminal region of 1, especially the phenylaminocarbonyl group (41), showed a remarkable increase in potency. Further improvement was observed by the attachment of the Glu residue to the meta-position of the phenyl ring of 41 (51). The ester derivative of 41 (56) had the ability to induce apoptosis which was dependent on the concentration of anti-Fas antibody in the colon cancer cell line, DLD-1, which expresses both Fas and FAP-1 and is resistant to Fas-induced apoptosis. We are now investigating whether FAP-1 is a main target of 56 and whether the inhibition of Fas/FAP-1 binding by 56 retrieves the apoptotic signal.

  DOI：

  10.1021/jm980617f
• 作为产物：
  描述：

  Z-Leu-Ala-OC2H5 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以92%的产率得到ethyl 2-(2-amino-4-methylpentanamido)propanoate
  参考文献：
  名称：

  A Selective Electrocatalytic Cleavage of the Benzyloxycarbonyl Group from Peptides

  摘要：

  描述了一种电合成方法，用于从保护氨基酸和肽中切断苄氧基碳酰基（benzyloxycarbonyl）基团。该方法基于在甲醇/醋酸中使用高比表面积的钯阴极，并在非常温和的条件下提供了优异的选择性。

  DOI：

  10.1055/s-1987-28191

文献信息

• The preparation of protected amines or alkylated amino acids
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0778285A1

  公开（公告）日：1997-06-11

  The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.

  本发明涉及一种制备受保护的胺或氨基酸的工艺。本发明还涉及生育酚自由基或由其衍生的自由基作为胺和氨基酸的保护基的用途，以及在该工艺中获得的作为中间体的化合物和制备二肽和寡肽的工艺。
• CASADEI, M. ANTONIETTA;PLETEHER, D., SYNTHESIS,(1987) N 12, 1118-1119
  作者：CASADEI, M. ANTONIETTA、PLETEHER, D.

  DOI：——

  日期：——
• Katakai,R., Journal of the Chemical Society. Perkin transactions I, 1979, p. 905 - 909
  作者：Katakai,R.

  DOI：——

  日期：——
• US5684132A
  申请人：——

  公开号：US5684132A

  公开（公告）日：1997-11-04
• US5767290A
  申请人：——

  公开号：US5767290A

  公开（公告）日：1998-06-16