tert-butyl N-(N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysyl)-N-benzylglycinate | 1582256-89-0

• 分子结构分类: 有机化合物
• 英文名称: tert-butyl N-(N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysyl)-N-benzylglycinate
• CAS: 1582256-89-0
• 化学式: C₃₉H₄₉N₃O₇
• 分子量: 671.834
• InChiKey: LEDAFANNXJGNGO-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysyl)-N-benzylglycinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Tailoring Cytotoxicity of Antimicrobial Peptidomimetics with High Activity against Multidrug-Resistant Escherichia coli

  摘要：

  Infections with multidrug-resistant pathogens are an increasing concern for public health. Recently, subtypes of peptide peptoid hybrids were demonstrated to display potent activity against multidrug-resistant Gram-negative bacteria. Here, structural variation of these antibacterial peptidomimetics was investigated as a tool for optimizing cell selectivity. A protocol based on dimeric building blocks allowed for efficient synthesis of an array of peptide peptoid oligomers representing length variation as well as different backbone designs displaying chiral or achiral peptoid residues. Lack of alpha-chirality in the side chains of the peptoid residues proved to be correlated to reduced cytotoxicity. Furthermore, optimization of the length of these peptidomimetics with an alternating cationic hydrophobic design was a powerful tool to enhance the selectivity against Gram-negative pathogens over benign mammalian cells. Thus, lead compounds with a high selectivity toward killing of clinically important multidrug-resistant E. coli were identified.

  DOI：

  10.1021/jm401335p
• 作为产物：
  描述：

  苄基甘氨酸叔丁酯 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 以62%的产率得到tert-butyl N-(N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysyl)-N-benzylglycinate
  参考文献：
  名称：

  Tailoring Cytotoxicity of Antimicrobial Peptidomimetics with High Activity against Multidrug-Resistant Escherichia coli

  摘要：

  Infections with multidrug-resistant pathogens are an increasing concern for public health. Recently, subtypes of peptide peptoid hybrids were demonstrated to display potent activity against multidrug-resistant Gram-negative bacteria. Here, structural variation of these antibacterial peptidomimetics was investigated as a tool for optimizing cell selectivity. A protocol based on dimeric building blocks allowed for efficient synthesis of an array of peptide peptoid oligomers representing length variation as well as different backbone designs displaying chiral or achiral peptoid residues. Lack of alpha-chirality in the side chains of the peptoid residues proved to be correlated to reduced cytotoxicity. Furthermore, optimization of the length of these peptidomimetics with an alternating cationic hydrophobic design was a powerful tool to enhance the selectivity against Gram-negative pathogens over benign mammalian cells. Thus, lead compounds with a high selectivity toward killing of clinically important multidrug-resistant E. coli were identified.

  DOI：

  10.1021/jm401335p