5''-O-triphenylmethyl-1,3,2',6',2''',6'''-hexa-N-(tertbutoxycarbonyl)neomycin B | 1292767-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5''-O-triphenylmethyl-1,3,2',6',2''',6'''-hexa-N-(tertbutoxycarbonyl)neomycin B
• CAS: 1292767-01-1
• 化学式: C₇₂H₁₀₈N₆O₂₅
• 分子量: 1457.67
• InChiKey: FXFJKNBKXALKJA-UWZOISTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  103.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  415.97
• 氢给体数：
  12.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  5''-O-triphenylmethyl-1,3,2',6',2''',6'''-hexa-N-(tertbutoxycarbonyl)neomycin B 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 6.0h， 以89%的产率得到6,3',4',2'',5'',4'''-hexa-O-acetyl-1,3,2',6',2''',6'''-hexa-N-(tertbutoxycarbonyl)-5''-O-triphenylmethyl neomycin B
  参考文献：
  名称：

  Synthesis and antibacterial activity of amphiphilic lysine-ligated neomycin B conjugates

  摘要：

  Amphiphilic lysine-ligated neomycin B building blocks were prepared by reductive amination of a protected C5 ''-modified neomycin B-based aldehyde and side chain-unprotected lysine or lysine-containing peptides. It was demonstrated that a suitably protected lysine-ligated neomycin B conjugate (NeoK) serves as a building block for peptide synthesis, enabling incorporation of aminoglycoside binding sites into peptides. Antibacterial testing of three amphiphilic lysine-ligated neomycin B conjugates against a representative panel of Gram-positive and Gram-negative strains demonstrates that C5 ''-modified neomycin-lysine conjugate retains antibacterial activity. However, in most cases the lysine-ligated neomycin B analogs display reduced potency against Gram-positive strains when compared to unmodified neomycin B or unligated peptide. An exception is MRSA where an eightfold enhancement was observed. When compared to unmodified neomycin B, the prepared lysine-neomycin conjugates exhibited a 4-8-fold enhanced Gram-negative activity against Pseudomonas aeruginosa and up to 12-fold enhanced activity was observed when compared to unligated reference peptides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.015
• 作为产物：
  描述：

  三苯基氯甲烷 、 hexa-N-Boc neomycin B 在 吡啶 作用下， 反应 10.0h， 以89%的产率得到5''-O-triphenylmethyl-1,3,2',6',2''',6'''-hexa-N-(tertbutoxycarbonyl)neomycin B
  参考文献：
  名称：

  Synthesis and antibacterial activity of amphiphilic lysine-ligated neomycin B conjugates

  摘要：

  Amphiphilic lysine-ligated neomycin B building blocks were prepared by reductive amination of a protected C5 ''-modified neomycin B-based aldehyde and side chain-unprotected lysine or lysine-containing peptides. It was demonstrated that a suitably protected lysine-ligated neomycin B conjugate (NeoK) serves as a building block for peptide synthesis, enabling incorporation of aminoglycoside binding sites into peptides. Antibacterial testing of three amphiphilic lysine-ligated neomycin B conjugates against a representative panel of Gram-positive and Gram-negative strains demonstrates that C5 ''-modified neomycin-lysine conjugate retains antibacterial activity. However, in most cases the lysine-ligated neomycin B analogs display reduced potency against Gram-positive strains when compared to unmodified neomycin B or unligated peptide. An exception is MRSA where an eightfold enhancement was observed. When compared to unmodified neomycin B, the prepared lysine-neomycin conjugates exhibited a 4-8-fold enhanced Gram-negative activity against Pseudomonas aeruginosa and up to 12-fold enhanced activity was observed when compared to unligated reference peptides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.015