| 1292767-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1292767-07-7
• 化学式: C₁₀₇H₁₅₄N₁₀O₃₉
• 分子量: 2204.44
• InChiKey: IMWLHCBGJJYEIF-TTXOUKSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  156.0
• 可旋转键数：
  35.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  608.66
• 氢给体数：
  9.0
• 氢受体数：
  39.0

反应信息

• 作为反应物：
  描述：

  N’-Boc-L-tryptophan benzyl ester 、 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以58%的产率得到
  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：

  C₁₁₄H₁₆₀N₁₀O₃₉ 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以87%的产率得到
  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