Fmoc-Trp-Pra-Pra-Trp-NHBn | 1134204-68-4

• 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: Fmoc-Trp-Pra-Pra-Trp-NHBn
• 英文别名: Fmoc-NH-(Boc)Trp-Pra-Pra-(Boc)Trp-NHBn
• CAS: 1134204-68-4
• 化学式: C₆₄H₆₅N₇O₁₀
• 分子量: 1092.26
• InChiKey: CBLHSUMYJLMISU-DLWBLUATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.67
• 重原子数：
  81.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  217.19
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,3,6',3''-tetra-N-(tert-butoxycarbonyl)-6''-azido-6''-deoxy-kanamycin A 、 Fmoc-Trp-Pra-Pra-Trp-NHBn 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 以83%的产率得到Fmoc-Trp(Boc)-β-alanyl-4-[[1,2,3]-triazol-1-yl-[(1,3,6',3''-tetra-N-(tert-butoxycarbonyl)-6''-deoxykanamycin)-6'']-(4-β-alanyl-4-[1,2,3]-triazol-1-yl-1,3,6',3''-tetra-N-(tert-butoxycarbonyl)-6''-deoxykanamycin)-6'']-Trp(Boc)-NHBn
  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：

  H2N-L-Trp(Boc)-NHBn 、 Fmoc-L-Trp(Boc)-NHBn 、 Fmoc-L-炔丙基甘氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Fmoc-Trp-Pra-Pra-Trp-NHBn
  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