1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-5''-(4-(β-alanyl(Fmoc)-Trp(Boc)-NHBn)-[1,2,3]-triazol-1-yl)-neomycin | 1134204-72-0

• 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: 1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-5''-(4-(β-alanyl(Fmoc)-Trp(Boc)-NHBn)-[1,2,3]-triazol-1-yl)-neomycin
• CAS: 1134204-72-0
• 化学式: C₉₆H₁₃₅N₁₃O₃₀
• 分子量: 1951.2
• InChiKey: AILVAWRMENLJPU-WRNYGFIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  139.0
• 可旋转键数：
  28.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  565.21
• 氢给体数：
  15.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-5''-(4-(β-alanyl(Fmoc)-Trp(Boc)-NHBn)-[1,2,3]-triazol-1-yl)-neomycin 、 三氟乙酸 反应 0.05h， 以90%的产率得到1,3,2',6',2''',6'''-hexaammonium-5''-(4-(β-alanyl(Fmoc)-Trp-NHBn)-[1,2,3]-triazol-1-yl)-5''-deoxyneomycin-hexakis(trifluoroacetate)
  参考文献：
  名称：

  Evaluation of amphiphilic aminoglycoside–peptide triazole conjugates as antibacterial agents

  摘要：

  The solid-and solution-phase synthesis of amphiphilic aminoglycoside-peptide triazole conjugates (APTCs) accessed by copper(I)-catalyzed 1,3-dipolar cycloaddition reaction between a hydrophobic and ultrashort peptide-based alkyne and a neomycin B-or kanamycin A-derived azide is presented. Antibacterial evaluation demonstrates that the antibacterial potency is affected by the nature of the peptide component. Several APTCs exhibit superior activity against neomycin B-and kanamycin A-resistant strains when compared to their parent aminoglycoside while displaying reduced activity against neomycin B-and kanamycin A-susceptible strains. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.116
• 作为产物：
  描述：

  5″-azide-1,3,2′,6′,2′″,6′″-hexa-N-(tert-butoxycarbonyl)-5″-deoxy-neomycin B 、 Fmoc-Pra-Trp-NHBn 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以87%的产率得到1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-5''-(4-(β-alanyl(Fmoc)-Trp(Boc)-NHBn)-[1,2,3]-triazol-1-yl)-neomycin
  参考文献：
  名称：

  Evaluation of amphiphilic aminoglycoside–peptide triazole conjugates as antibacterial agents

  摘要：

  The solid-and solution-phase synthesis of amphiphilic aminoglycoside-peptide triazole conjugates (APTCs) accessed by copper(I)-catalyzed 1,3-dipolar cycloaddition reaction between a hydrophobic and ultrashort peptide-based alkyne and a neomycin B-or kanamycin A-derived azide is presented. Antibacterial evaluation demonstrates that the antibacterial potency is affected by the nature of the peptide component. Several APTCs exhibit superior activity against neomycin B-and kanamycin A-resistant strains when compared to their parent aminoglycoside while displaying reduced activity against neomycin B-and kanamycin A-susceptible strains. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.116