N-Z-D-valyl-leucine | 74202-02-1

• 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: N-Z-D-valyl-leucine
• 英文别名: Cbz-D-Val-Leu-OH；N-benzyloxycarbonyl-D-valyl-L-leucine；((Benzyloxy)carbonyl)-D-valyl-L-leucine；(2S)-4-methyl-2-[[(2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoic acid
• CAS: 74202-02-1
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: ABNKBDCDDUXJCU-JKSUJKDBSA-N

物化性质

• 熔点：
  130-133 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  590.1±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Z-D-valyl-leucine 在 N-乙基吗啉 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 30.0h， 生成 N-Z-D-valyl-leucyl-N^ε-Z-lysine p-nitroanilide
  参考文献：
  名称：

  Martynov, V. F.; Pozdnev, V. F.; Smirnov, A. O., Journal of general chemistry of the USSR, 1990, vol. 60, # 2.2, p. 391 - 395

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-D-缬氨酸 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 1,4-二氧六环 、 吡啶 、 水 为溶剂， 反应 40.0h， 生成 N-Z-D-valyl-leucine
  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

• 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。
• MARTYNOV, V. F.;POZDNEV, V. F.;SMIRNOV, A. O.;SOROCHINSKAYA, E. I., ZH. OBSHCH. XIMII, 60,(1990) N, S. 451-455
  作者：MARTYNOV, V. F.、POZDNEV, V. F.、SMIRNOV, A. O.、SOROCHINSKAYA, E. I.

  DOI：——

  日期：——
• US4257940A
  申请人：——

  公开号：US4257940A

  公开（公告）日：1981-03-24
• 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.
• Martynov, V. F.; Pozdnev, V. F.; Smirnov, A. O., Journal of general chemistry of the USSR, 1990, vol. 60, # 2.2, p. 391 - 395
  作者：Martynov, V. F.、Pozdnev, V. F.、Smirnov, A. O.、Sorochinskaya, E. I.

  DOI：——

  日期：——