Boc-Ala-Lys(Z)-OBzl | 114856-02-9

• 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: Boc-Ala-Lys(Z)-OBzl
• 英文别名: Boc-Ala-Lys(Z)-OBn；benzyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 114856-02-9
• 化学式: C₂₉H₃₉N₃O₇
• 分子量: 541.645
• InChiKey: PYIHUKAUPAMMBO-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  132.06
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Lys(Z)-OBzl 在 盐酸 、 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 52.33h， 生成
  参考文献：
  名称：

  NOVEL COMPOUND WITH EFFECTS OF THROMBOLYSIS, FREE RADICAL SCAVENGING AND THROMBUS-TARGETING AS WELL AS PREPARATION METHOD AND USE THEREOF

  摘要：

  本发明公开了一种具有溶栓、清除自由基和靶向血栓作用的新型化合物，以及其制备方法和用途。该化合物是通过连接臂将溶栓肽、自由基清除剂和靶向/抗血栓肽结合在一起形成的三元共轭物。本发明还公开了含有这些化合物的药物组合物，其中这些化合物形成纳米球状结构。

  公开号：

  US20150290339A1
• 作为产物：
  描述：

  N-α-tert-Butyloxycarbonyl-N-ε-carbobenzoxy-L-lysine benzyl ester 在 N-甲基吗啉 、 TFA-anisole 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 Boc-Ala-Lys(Z)-OBzl
  参考文献：
  名称：

  Synthesis of deacetyl-thymosin .BETA.7 and examination of its immunological effect on the blastogenic response of T-lymphocytes of a uremic patient with cell-mediated immunodeficiency.

  摘要：

  通过叠氮化物组装几个多肽片段，随后在二甲基硒存在下用1 M三氟甲磺酸-硫代苯甲醚于三氟乙酸中脱保护，合成了对应于去乙酰胸腺β7整个氨基酸序列的未四十一肽。对合成的多肽在一位尿毒症患者中对植物血凝素刺激的T淋巴细胞的受损母细胞转化反应的影响进行了测试。发现合成的多肽具有恢复T淋巴细胞受损母细胞转化反应的活性。

  DOI：

  10.1248/cpb.36.700

文献信息

• Synthesis and Biological Activity of Nitronyl Nitroxide Containing Peptides
  作者：Ming Zhao、Junling Liu、Chao Wang、Lili Wang、Hu Liu、Shiqi Peng

  DOI：10.1021/jm050050k

  日期：2005.6.1

  [1-(1 ',3 '-Dioxyl-4 ',4 ',5 ',5 '-tetramethyldihydroimidazol-2-yl)-phenyl-4-yl]oxyacetic acid (4), a nitronyl nitroxide, and its peptide derivatives, N-[1-(1 ',3 '-dioxyl-4 ',4 ',5 ',5 '-tetramethyldihydroimidazol-2-yl)-phenyl-4-yl]oxyacetyl-ARPAK (9a), -GRPAK (9b), and -QRPAK (9c), were synthesized and characterized. Judging from the results of electron spin resonance analysis, the newly synthesized nitronyl nitroxide containing peptides, 9a, 9b, and 9c, demonstrated the characteristics of free radicals. The free radical scavenging activities of 9a, 9b, and 9c were assessed using in vitro free radical scavenging tests. The thrombolysis effect of 9a, 9b, and 9c was evaluated using an euglobulin clot lysis test, a fibrinolytic lysis test, and in vivo thrombolysis tests. Results indicated that these nitronyl nitroxide containing peptides possessed both free radical scavenging activity and thrombolytic activity.
• Zhao, Ming; Peng, Shiqi, Advanced Synthesis and Catalysis, 1999, vol. 341, # 7, p. 668 - 676
  作者：Zhao, Ming、Peng, Shiqi

  DOI：——

  日期：——
• A new class of β-carboline alkaloid-peptide conjugates with therapeutic efficacy in acute limb ischemia/reperfusion injury
  作者：Wei Bi、Yue Bi、Ping Xue、Yanrong Zhang、Xiang Gao、Zhibo Wang、Meng Li、Michèle Baudy-Floc’h、Nathaniel Ngerebara、K. Michael Gibson、Lanrong Bi

  DOI：10.1016/j.ejmech.2011.01.021

  日期：2011.5

  We describe a novel class of beta-carboline alkaloid-peptide conjugates that possess both free radical scavenging and thrombolytic activity. These conjugates demonstrate therapeutic efficacy in a rat arterial thrombosis assay, as well as free radical scavenging capacity as evaluated in a PC12 cell survival assay. Our results indicate that beta-carboline alkaloid-peptide conjugate 26a exerts a significant protective effect against local and remote organ injury induced by limb I/R injury in the rat. Published by Elsevier Masson SAS.
• The composition and sequence specificity of Pro-Ala-Lys-OH for the thrombolytic activities of P6A and related oligopeptides
  作者：Ming Zhao、Chao Wang、Jiangyuan Liu、Kexiang Zhou、Shiqi Peng

  DOI：10.1016/j.bmc.2004.02.011

  日期：2004.5

  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.
• Identification, synthesis and bioassay for the metabolites of P6A
  作者：Ming Zhao、Chao Wang、Jian Yang、Jiangyuan Liu、Youxuan Xu、Yanfen Wu、Shiqi Peng

  DOI：10.1016/j.bmc.2003.09.021

  日期：2003.11

  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.