Cbz-D-Val-Leu-O-Me | 55790-11-9

• 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: Cbz-D-Val-Leu-O-Me
• 英文别名: N-benzyloxycarbonyl-D-valyl-L-leucine methyl ester；Benzyloxycarbonyl-D-valyl-L-leucine methylester；methyl (2S)-4-methyl-2-[[(2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoate
• CAS: 55790-11-9
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: PKLDYUWADSNDGB-DLBZAZTESA-N

物化性质

• 沸点：
  536.1±40.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz-D-Val-Leu-O-Me 在 sodium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以66%的产率得到N-Z-D-valyl-leucine
  参考文献：
  名称：

  Valylleucyllysine derivatives, process for producing same and method for

  摘要：

  由以下公式表示的一种缬氨酸赖氨酰赖氨酸衍生物，其中R.sub.1代表氢或苯甲酰，R.sub.2代表萘基。上述化合物可作为各种酶（如胰蛋白酶、纤溶酶、卡利克雷因、尿激酶、Cl-酯酶等）的优良底物。因此，可以通过使用该化合物作为底物来测量酶的活性。

  公开号：

  US04257940A1
• 作为产物：
  描述：

  D-缬氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 73.0h， 生成 Cbz-D-Val-Leu-O-Me
  参考文献：
  名称：

  Synthesis and functional evaluation of a peptide derivative of 1-.beta.-D-arabinofuranosylcytosine

  摘要：

  We have synthesized a peptidyl prodrug derivative of 1-beta-D-arabinofuranosylcytosine (1) designed to be a selective substrate of plasmin. D-Val-Leu-Lys-ara-C (2) was obtained by coupling the protected peptide Cbz-D-Val-Leu-(N6-Cbz)Lys-OH and ara-C (1) by a water-soluble carbodiimide (EDCI), followed by the removal of the Cbz groups by using catalytic hydrogenolysis over Pd/C. The kinetic constant of hydrolysis of 2 in the presence of plasmin demonstrated effective release of 1. The amino group of 1, which is sensitive to the removal by cytidine deaminase, is protected in 2 by the formation of the amide bond resulting in a prolonged half-life of 2 in biological milieu. The antiproliferative efficiency of 2 against L1210 leukemic cells was significantly higher than that of 1. The activity of 2 was abolished in the presence of serine proteinase inhibitor, (4-amidinopheny)methanesulfonyl fluoride. These data indicate that 2 is a prodrug form of 1 in systems generating plasmin.

  DOI：

  10.1021/jm00096a006

文献信息

• Etude de la racemisation induite par la dmap dans les reactions de couplage peptidique
  作者：Jean-Paul Gamet、Robert Jacquier、Jean verducci

  DOI：10.1016/s0040-4020(01)88439-8

  日期：1984.1

  with H-hydroxybenzotriazole (HOBt). The activation of N-acylated aminoacids by the means of DMAP leads to a complete racemization. On the other hand, for the aminoacids protected under their urethans derivatives, DMAP gives better yields than HOBt with racemization extent generally equal to or slightly higer to that observed with HOBt.

  研究了在肽合成中使用4-二甲基氨基吡啶（DMAP）作为碳二亚胺添加剂的范围和局限性，并与H-羟基苯并三唑（HOBt）获得的结果进行了比较。通过DMAP活化N-酰化的氨基酸导致完全消旋。另一方面，对于在其氨基甲酸酯衍生物保护下的氨基酸，DMAP的收率比HOBt好，外消旋程度通常等于或略高于HOBt。
• US4257940A
  申请人：——

  公开号：US4257940A

  公开（公告）日：1981-03-24
• Valylleucyllysine derivatives, process for producing same and method for
  申请人：Torii & Co., Ltd.

  公开号：US04257940A1

  公开（公告）日：1981-03-24

  A valylleucyllysine derivative represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen or benzoyl and R.sub.2 represented naphthyl. The above compound is useful as an excellent substrate for various anzymes, such as, trypsin, plasmin, kallikrein, urokinase, Cl-esterase and the like. Accordingly, the activity of enzymes can be measured by use of said compound as a substrate.

  由以下公式表示的一种缬氨酸赖氨酰赖氨酸衍生物，其中R.sub.1代表氢或苯甲酰，R.sub.2代表萘基。上述化合物可作为各种酶（如胰蛋白酶、纤溶酶、卡利克雷因、尿激酶、Cl-酯酶等）的优良底物。因此，可以通过使用该化合物作为底物来测量酶的活性。
• Synthesis and functional evaluation of a peptide derivative of 1-.beta.-D-arabinofuranosylcytosine
  作者：Zoltan Balajthy、Janos Aradi、Ildiko T. Kiss、Pal Elodi

  DOI：10.1021/jm00096a006

  日期：1992.9

  We have synthesized a peptidyl prodrug derivative of 1-beta-D-arabinofuranosylcytosine (1) designed to be a selective substrate of plasmin. D-Val-Leu-Lys-ara-C (2) was obtained by coupling the protected peptide Cbz-D-Val-Leu-(N6-Cbz)Lys-OH and ara-C (1) by a water-soluble carbodiimide (EDCI), followed by the removal of the Cbz groups by using catalytic hydrogenolysis over Pd/C. The kinetic constant of hydrolysis of 2 in the presence of plasmin demonstrated effective release of 1. The amino group of 1, which is sensitive to the removal by cytidine deaminase, is protected in 2 by the formation of the amide bond resulting in a prolonged half-life of 2 in biological milieu. The antiproliferative efficiency of 2 against L1210 leukemic cells was significantly higher than that of 1. The activity of 2 was abolished in the presence of serine proteinase inhibitor, (4-amidinopheny)methanesulfonyl fluoride. These data indicate that 2 is a prodrug form of 1 in systems generating plasmin.