(S)-2-((S)-2-Amino-3-biphenyl-4-yl-propionylamino)-5-guanidino-pentanoic acid benzylamide | 753451-18-2

• 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: (S)-2-((S)-2-Amino-3-biphenyl-4-yl-propionylamino)-5-guanidino-pentanoic acid benzylamide
• 英文别名: H-Bip-Arg-NHBn；(2S)-2-[[(2S)-2-amino-3-(4-phenylphenyl)propanoyl]amino]-N-benzyl-5-(diaminomethylideneamino)pentanamide
• CAS: 753451-18-2
• 化学式: C₂₈H₃₄N₆O₂
• 分子量: 486.617
• InChiKey: PGRFMNLBCCYOON-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-Amino-3-biphenyl-4-yl-propionylamino)-5-guanidino-pentanoic acid benzylamide 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 L-arginyl-L-4,4'-biphenylalanyl-L-arginine benzylamide
  参考文献：
  名称：

  Albumin Binding of Short Cationic Antimicrobial Micropeptides and Its Influence on the in Vitro Bactericidal Effect

  摘要：

  The interactions between a range of small cationic antibacterial tripeptides and bovine and human serum albumin in a buffered aqueous solution at 25 degrees C have been studied using isothermal titration calorimetry. Results from the binding study indicate a single binding site on albumin with a dissociation constant between 4.3 and 22.2 mu M for the different peptides. In a theoretical mouse model, a dissociation constant in this range corresponds to 95% albumin binding. The effect of this albumin interaction on the antibacterial capacity of the peptides against Staphylococcus aureus, strain ATCC 25923 was studied by including albumin in the assays at a 0.55 mM concentration. Presence of albumin induced a 10-fold increase of the minimal inhibitory concentration for the bulk of the peptides. Albumin itself has no effect on the bacterial growth and this increase is entirely ascribed to a strong competing protein binding. Collectively these results indicate that these antibacterial peptides do bind to albumin and that this binding strongly reduces the effective concentration of peptides available to combat bacteria.

  DOI：

  10.1021/jm0703542
• 作为产物：
  描述：

  N1-benzyl-(2S)-2-amino-5-amino(imino)methylaminopentanamide 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-((S)-2-Amino-3-biphenyl-4-yl-propionylamino)-5-guanidino-pentanoic acid benzylamide
  参考文献：
  名称：

  Albumin Binding of Short Cationic Antimicrobial Micropeptides and Its Influence on the in Vitro Bactericidal Effect

  摘要：

  The interactions between a range of small cationic antibacterial tripeptides and bovine and human serum albumin in a buffered aqueous solution at 25 degrees C have been studied using isothermal titration calorimetry. Results from the binding study indicate a single binding site on albumin with a dissociation constant between 4.3 and 22.2 mu M for the different peptides. In a theoretical mouse model, a dissociation constant in this range corresponds to 95% albumin binding. The effect of this albumin interaction on the antibacterial capacity of the peptides against Staphylococcus aureus, strain ATCC 25923 was studied by including albumin in the assays at a 0.55 mM concentration. Presence of albumin induced a 10-fold increase of the minimal inhibitory concentration for the bulk of the peptides. Albumin itself has no effect on the bacterial growth and this increase is entirely ascribed to a strong competing protein binding. Collectively these results indicate that these antibacterial peptides do bind to albumin and that this binding strongly reduces the effective concentration of peptides available to combat bacteria.

  DOI：

  10.1021/jm0703542