Nα-benzoyl-L-lysinamide | 10139-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Nα-benzoyl-L-lysinamide
• 英文别名: N^α-benzoyl-L-lysine amide；N^α-Benzoyl-L-lysin-amid；Benzoyl-L-lysinamid；N-[(2S)-1,6-diamino-1-oxohexan-2-yl]benzamide
• CAS: 10139-85-2
• 化学式: C₁₃H₁₉N₃O₂
• 分子量: 249.313
• InChiKey: KOUTUYBOJSFSCO-NSHDSACASA-N

物化性质

• 沸点：
  548.4±45.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-双(苄氧基)苯甲酸 、 Nα-benzoyl-L-lysinamide 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以49%的产率得到(S)-2-benzoylamino-6-[(2,3-dibenzyloxybenzoyl)amino]hexanoamide
  参考文献：
  名称：

  Synthesis and evaluation of myxochelin analogues as antimetastatic agents

  摘要：

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.040
• 作为产物：
  描述：

  Nα-benzoyl-Nε-tert-butoxycarbonyl-L-lysinamide 在 盐酸 、 水 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以71%的产率得到Nα-benzoyl-L-lysinamide
  参考文献：
  名称：

  Synthesis and evaluation of myxochelin analogues as antimetastatic agents

  摘要：

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.040

文献信息

• Process for semi-synthesis of human insulin and alkaline protease for use therein
  申请人：WAKO PURE CHEMICAL INDUSTRIES, LTD.

  公开号：EP0092829A2

  公开（公告）日：1983-11-02

  A process is described for semi-synthesis of human insulin by preparing human insulin derivative containing carboxyl group-protected threonine at B30 thereof from porcine insulin, using water as a reaction solvent and lysyl end peptidase produced from Achromobacter lyticus as a catalyst. There is also disclosed a new protease isolated from the genus Achromobacter.

  本研究描述了一种半合成人胰岛素的工艺，即以猪胰岛素为原料，以水为反应溶剂，以从溶菌 Achromobacter lyticus 中提取的溶菌末肽酶为催化剂，制备出含有羧基保护的苏氨酸 B30 的人胰岛素衍生物。 此外，还公开了一种从 Achromobacter 菌属分离出来的新型蛋白酶。
• Process for semi-synthesis of human insulin, water-soluble cross-linked Achromobacter protease I for use therein and a process for preparing the same
  申请人：WAKO PURE CHEMICAL INDUSTRIES, LTD.

  公开号：EP0367302A2

  公开（公告）日：1990-05-09

  A water-soluble cross-linked Achromobacter protease I with a molecular weight from 400,000 to 700,000 is described. Said enzyme is used in a process for semi-synthesizing human insulin.

  描述了一种分子量为 400,000 至 700,000 的水溶性交联 Achromobacter 蛋白酶 I。所述酶用于半合成人胰岛素的工艺中。
• Substrates for tafi (a)
  申请人：Ziegler Hugo

  公开号：US20060068457A1

  公开（公告）日：2006-03-30

  The invention relates to compounds of general formula (I) and acid addition salts thereof, where the various symbols have the meanings given in the description and claims, the production and use thereof as substrate for the detection of TAFIa, a fibrinolysis inhibiting enzyme. The detection occurs by using the absorption between 400 and 412 nm, arising as a result of the formation of 3-carboxy-4-nitrothiophenol from Ellman's reagent as a function of time.

  本发明涉及通式(I)的化合物及其酸加成盐，其中各种符号的含义见说明书和权利要求书，本发明还涉及用其生产和用作检测纤维蛋白溶解抑制酶 TAFIa 的底物。检测方法是利用埃尔曼试剂中 3-羧基-4-硝基苯硫酚的形成随时间变化而产生的 400 至 412 纳米之间的吸收。
• Bergmann; Zervas; Ross, Journal of Biological Chemistry, 1935, vol. 111, p. 245,251
  作者：Bergmann、Zervas、Ross

  DOI：——

  日期：——
• Hofmann; Bergmann, Journal of Biological Chemistry, 1939, vol. 130, p. 81,85
  作者：Hofmann、Bergmann

  DOI：——

  日期：——