N-acetyl-L-alanyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-L-alanine | 1320346-06-2

• 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: N-acetyl-L-alanyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-L-alanine
• 英文别名: (2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-acetamidopropanoyl]amino]-6-[[2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetyl]amino]hexanoyl]amino]acetyl]amino]-6-[[2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetyl]amino]hexanoyl]amino]acetyl]amino]-6-[[2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetyl]amino]hexanoyl]amino]propanoic acid
• CAS: 1320346-06-2
• 化学式: C₇₂H₁₀₄N₁₀O₃₀
• 分子量: 1589.67
• InChiKey: OQCMLJXJOPCREE-JWTXZYLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  112
• 可旋转键数：
  44
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  626
• 氢给体数：
  23
• 氢受体数：
  30

反应信息

• 作为产物：
  描述：

  [4-(α-D-mannopyranosyloxy)phenyl]acetic acid 、 N-acetyl-L-alanyl-L-lysyl-glycyl-L-lysyl-glycyl-L-lysyl-L-alanine 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以25%的产率得到N-acetyl-L-alanyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-glycyl-L-lysyl-Nε-{4-[(α-D-mannopyranosyloxy)phenyl]acetamido}-L-alanine
  参考文献：
  名称：

  Bi- and trivalent glycopeptide mannopyranosides as inhibitors of type 1 fimbriae-mediated bacterial adhesion: variation of valency, aglycon and scaffolding

  摘要：

  In order to test relevant structural parameters for effective inhibition of mannose-specific bacterial adhesion, bi- and trivalent glycopeptide alpha-D-mannopyranosides were synthesized that differ in their conformational properties as well as in the spatial arrangement of attached mannosyl residues. They were tested in an inhibition adhesion assay with fluorescent Escherichia coli bacteria and testing results were referenced to the inhibitory potency of methyl alpha-D-mannopyranoside. It was shown, that besides the nature of the mannoside aglycon moiety, scaffolding of alpha-D-mannopyranosides on a peptide backbone was important for the performance of the synthesized glycopeptides as inhibitors of bacterial adhesion. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.023