Ac-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-NH2 | 1392101-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Ac-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-NH2
• 英文别名: (2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[[(2S)-2-[3-[acetyl(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanoyl]-(4-aminobutyl)amino]propanoylamino]-3-phenylpropanamide
• CAS: 1392101-15-3
• 化学式: C₁₃₀H₁₈₉N₂₅O₁₇
• 分子量: 2374.09
• InChiKey: REMNUVQQDCTRSU-UKWJOZPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  172
• 可旋转键数：
  88
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  647
• 氢给体数：
  17
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  3-({4-[(tert-butoxycarbonyl)amino]butyl}[(9H-fluoren-9-ylmethoxy)carbonyl]amino)propanoic acid 、 Fmoc-L-苯丙氨酸 、 乙酸酐 在 哌啶 、 N-羟基-7-氮杂苯并三氮唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以13%的产率得到Ac-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-N(BuNH2)bAla-Phe-NH2
  参考文献：
  名称：

  Antimicrobial Activity of Peptidomimetics against Multidrug-Resistant Escherichia coli: A Comparative Study of Different Backbones

  摘要：

  Novel remedies in the battle against multidrug-resistant bacterial strains are urgently needed, and one obvious approach involves antimicrobial peptides and mimics hereof. The impact of alpha- and beta-peptoid as well as beta(3)-amino acid modifications on the activity profile against beta-lactamase-producing Escherichia coli was assessed by testing an array comprising different types of cationic peptidomimetics obtained by a general monomer-based solid-phase synthesis protocol. Most of the peptidomimetics possessed high to moderate activity toward multidrug-resistant E. coli as opposed to the corresponding inactive peptides. Nevertheless, differences in hemolytic activities indicate that a careful choice of backbone design constitutes a significant parameter in the search for effective cationic antimicrobial peptidomimetics targeting specific bacteria.

  DOI：

  10.1021/jm300820a

文献信息

• Antimicrobial Activity of Peptidomimetics against Multidrug-Resistant Escherichia coli: A Comparative Study of Different Backbones
  作者：Rasmus D. Jahnsen、Niels Frimodt-Møller、Henrik Franzyk

  DOI：10.1021/jm300820a

  日期：2012.8.23

  Novel remedies in the battle against multidrug-resistant bacterial strains are urgently needed, and one obvious approach involves antimicrobial peptides and mimics hereof. The impact of alpha- and beta-peptoid as well as beta(3)-amino acid modifications on the activity profile against beta-lactamase-producing Escherichia coli was assessed by testing an array comprising different types of cationic peptidomimetics obtained by a general monomer-based solid-phase synthesis protocol. Most of the peptidomimetics possessed high to moderate activity toward multidrug-resistant E. coli as opposed to the corresponding inactive peptides. Nevertheless, differences in hemolytic activities indicate that a careful choice of backbone design constitutes a significant parameter in the search for effective cationic antimicrobial peptidomimetics targeting specific bacteria.