Boc-Glu(Asp-Arg)-Asp-Arg | 1043921-44-3

• 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-Glu(Asp-Arg)-Asp-Arg
• CAS: 1043921-44-3
• 化学式: C₃₀H₅₁N₁₁O₁₄
• 分子量: 789.8
• InChiKey: YRBSSVLCKBBNDO-ATIWLJMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.76
• 重原子数：
  55.0
• 可旋转键数：
  25.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  427.73
• 氢给体数：
  15.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Boc-Glu(Asp-Arg)-Asp-Arg 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(2S)-2-[[(2S)-2-[[(4S)-4-amino-5-[[(2S)-3-carboxy-1-[[(1S)-1-carboxy-4-(diaminomethylideneamino)butyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoyl]amino]-3-carboxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
  参考文献：
  名称：

  Synthesis, nano-scale assembly, and in vivo anti-thrombotic activity of novel short peptides containing l-Arg and l-Asp or l-Glu

  摘要：

  Two tripeptides H-Asp(Arg)-Arg (3a) and H-Glu(Arg)-Arg (3b), four pentapeptides H-Asp(Arg-Asp)-Arg-Asp (6a), H-Glu(Arg-Asp)-Arg-Asp (6b), H-Asp(Asp-Arg)-Asp-Arg (10a), and H-Glu(Asp-Arg)-Asp-Arg (10b), and their Cu(II)-peptide complexes Cu(II)-Asp(Arg)-Arg [3a-Cu(II)], Cu(II)-Glu(Arg)-Arg [3b-Cu(II)], Cu(II)-Asp(Arg-Asp)-Arg-Asp [6a-Cu(II)], Cu(II)-Glu(Arg-Asp)-Arg-Asp [6b-Cu(II)], Cu(II)-Asp(Asp-Arg)-Asp-Arg [10a-Cu(II)], and Cu(II)-Glu(Asp-Arg)-Asp-Arg [10b Cu( II)] were designed and synthesized. Their self-assembling properties and in vivo anti-thrombotic activities were investigated. In normal saline (NS), the Cu(II)-peptide complexes assembled into stable nano-particles surrounded by negative charges (-4.102 to -9.825 mV), with diameters ranging from 212.1 +/- 4.0 to 632.4 +/- 36.7 nm. TEM analysis exhibited that the compounds remained as nano-globes in the solid state, with diameters ranging from 15 to 20 nm. In an in vivo anti-thrombotic assay, peptides (3,6,10) a, b at 5 mu mol/kg reduced the thrombus weights of a rat model by 15-40%. Aspirin, a widely used anti-thrombotic drug, achieved comparable activity in this model system at a dosage of ca. 110 mu mol/kg. The required dosage of Cu(II)-peptide complexes [(3,6,10) a, b]-Cu(II), which assemble into stable nano-particles, was significantly reduced to 0.05 mu mol/kg. Therefore, the antithrombotic activity of the nano-particles [(3,6,10) a, b] -Cu(II) increased dramatically by 100-fold over that of the corresponding peptides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.064
• 作为产物：
  描述：

  Boc-Glu[Asp(OMe)-Arg-OMe]-Asp(OMe)-Arg-OMe 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到Boc-Glu(Asp-Arg)-Asp-Arg
  参考文献：
  名称：

  Synthesis, nano-scale assembly, and in vivo anti-thrombotic activity of novel short peptides containing l-Arg and l-Asp or l-Glu

  摘要：

  Two tripeptides H-Asp(Arg)-Arg (3a) and H-Glu(Arg)-Arg (3b), four pentapeptides H-Asp(Arg-Asp)-Arg-Asp (6a), H-Glu(Arg-Asp)-Arg-Asp (6b), H-Asp(Asp-Arg)-Asp-Arg (10a), and H-Glu(Asp-Arg)-Asp-Arg (10b), and their Cu(II)-peptide complexes Cu(II)-Asp(Arg)-Arg [3a-Cu(II)], Cu(II)-Glu(Arg)-Arg [3b-Cu(II)], Cu(II)-Asp(Arg-Asp)-Arg-Asp [6a-Cu(II)], Cu(II)-Glu(Arg-Asp)-Arg-Asp [6b-Cu(II)], Cu(II)-Asp(Asp-Arg)-Asp-Arg [10a-Cu(II)], and Cu(II)-Glu(Asp-Arg)-Asp-Arg [10b Cu( II)] were designed and synthesized. Their self-assembling properties and in vivo anti-thrombotic activities were investigated. In normal saline (NS), the Cu(II)-peptide complexes assembled into stable nano-particles surrounded by negative charges (-4.102 to -9.825 mV), with diameters ranging from 212.1 +/- 4.0 to 632.4 +/- 36.7 nm. TEM analysis exhibited that the compounds remained as nano-globes in the solid state, with diameters ranging from 15 to 20 nm. In an in vivo anti-thrombotic assay, peptides (3,6,10) a, b at 5 mu mol/kg reduced the thrombus weights of a rat model by 15-40%. Aspirin, a widely used anti-thrombotic drug, achieved comparable activity in this model system at a dosage of ca. 110 mu mol/kg. The required dosage of Cu(II)-peptide complexes [(3,6,10) a, b]-Cu(II), which assemble into stable nano-particles, was significantly reduced to 0.05 mu mol/kg. Therefore, the antithrombotic activity of the nano-particles [(3,6,10) a, b] -Cu(II) increased dramatically by 100-fold over that of the corresponding peptides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.064