Boc-Ala-Arg(NO2)-Pro-Ala-OBzl | 663954-92-5

• 英文名称: Boc-Ala-Arg(NO2)-Pro-Ala-OBzl
• 英文别名: Boc-Ala-Arg(NO2)-Pro-Ala-OBn
• CAS: 663954-92-5
• 化学式: C₂₉H₄₄N₈O₉
• 分子量: 648.717
• InChiKey: PNTKCDCYRJIJCN-LGGPRVQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  234.19
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Arg(NO2)-Pro-Ala-OBzl 在 palladium on activated charcoal sodium hydroxide 、 甲酸 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.0h， 生成 Ala-Arg-Pro-Ala-Arg-OH
  参考文献：
  名称：

  The composition and sequence specificity of Pro-Ala-Lys-OH for the thrombolytic activities of P6A and related oligopeptides

  摘要：

  The in vitro and in vivo thrombolytic activities of Ala-Arg-Pro-Ala-Lys-OH, its analogs and the related peptides were assayed. The results indicate that when (5)Lys of Ala-Arg-Pro-Ala-Lys-OH is changed into (5)Arg, and (5)Lys of Pro-Ala-Lys-OH is changed into (3)Arg the thrombolytic activities are collapsed; when Pro-Ala-Lys-OH is changed into Ala-Pro-Lys-OH, and Ala-Arg-Pro-Ala-Lys-OH is changed into Ala-Arg-Ala-Pro-Lys-OH the thrombolytic activities are also collapsed; when (5)nLys of Ala-Arg-Pro-Ala-Lys-OH is changed into (5)nLeu the thrombolytic activities are again collapsed. All of the results indicate that for the thrombolytic activities of Ala-Arg-Pro-Ala-Lys-OH and the related peptides Pro-Ala-Lys-OH exhibits either amino acid composition specificity or sequence specificity. The composition and sequence specificity of Pro-Ala-Lys-OH reflects its rule as the pharmacophore of P6A and the related peptides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.011
• 作为产物：
  描述：

  Boc-Arg(NO2)-Pro-OBzl 在 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 101.0h， 生成 Boc-Ala-Arg(NO2)-Pro-Ala-OBzl
  参考文献：
  名称：

  Identification, synthesis and bioassay for the metabolites of P6A

  摘要：

  The metabolites Ala-Arg-Pro-Ala-OH, Ala-Arg-Pro-OH, Arg-Pro-Ala-Lys-OH and Pro-Ala-Lys-OH were identified by HPLC/ESI/MS from the in vivo blood of Ala-Arg-Pro-Ala-Lys-OH (M) received mice. The in vitro incubation of P6A in the blood of mice the same metabolites were also found by use of the Prep LC System. The protective intermediates of these metabolites were prepared via the solution method using the stepwise synthesis in 77.4, 90, 88, and 80% yield, respectively. After deprotection with catalytic hydrogenation the intermediates were converted into the corresponding sequences Arg-Pro-Ala-Lys-OH Pro-Ala-Lys-OH, Ala-Arg-Pro-Ala-OH, and Ala-Arg-Pro-OH in 90, 95, 85% and 86% yield, respectively. In the thrombolysis in vivo assay the synthetic Ala-Arg-Pro-Ala-OH, and Ala-Arg-Pro-OH exhibited no activity. On the other hand the thrombolytic activity of Arg-Pro-Ala-Lys-OH was comparable to P6A, and an enhanced thrombolytic activity was observed for Pro-Ala-Lys-OH. In the in vitro fibrinolytic lysis tests the approximate results were obtained and an enhanced activity was also observed for Pro-Ala-Lys-OH. In the euglobulin clot lysis time tests P6A, Arg-Pro-Ala-Lys-OH and Pro-Ala-Lys-OH gave significantly shorter time than that given by UK, demonstrating their fast action. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.021