1,4-bis((1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)methoxy)benzene | 1402053-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis((1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)methoxy)benzene
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[4-[[4-[[1-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methoxy]phenoxy]methyl]triazol-1-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1402053-99-9
• 化学式: C₂₈H₃₈N₈O₁₂
• 分子量: 678.656
• InChiKey: NRXNPBFRKBDNJH-AZMCGPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  278
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 以88%的产率得到1,4-bis((1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)methoxy)benzene
  参考文献：
  名称：

  Synthesis of bivalent glycoclusters containing GlcNAc as hexasaccharide mimetics. Bactericidal activity against Helicobacter pylori

  摘要：

  The Cu(I) catalysed cycloaddition reaction of azides and alkynes has been used to generate a series of divalent GlcNAc clusters with both alpha and beta configurations. These glycoclusters can be considered as potential mimetics of an anti Helicobacter pylori hexasaccharide as they present two GlcNAc residues grafted onto a core scaffold. Two bivalent compounds based on alpha-O-GlcNAc were identified that selectively reduced the viability of H. pylori. These compounds showed activity towards different strains of H. pylori (Pu4 vs P12). The activity of the oligosaccharide mimetics is speculated to be due to the GlcNAc residues being able to adopt spatial arrangements accessible to the anti H. pylori hexasaccharide which may be important for activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.07.011

文献信息

• Synthesis of bivalent glycoclusters containing GlcNAc as hexasaccharide mimetics. Bactericidal activity against Helicobacter pylori
  作者：Dandan Yan、Julie Naughton、Marguerite Clyne、Paul V. Murphy

  DOI：10.1016/j.carres.2012.07.011

  日期：2012.10

  The Cu(I) catalysed cycloaddition reaction of azides and alkynes has been used to generate a series of divalent GlcNAc clusters with both alpha and beta configurations. These glycoclusters can be considered as potential mimetics of an anti Helicobacter pylori hexasaccharide as they present two GlcNAc residues grafted onto a core scaffold. Two bivalent compounds based on alpha-O-GlcNAc were identified that selectively reduced the viability of H. pylori. These compounds showed activity towards different strains of H. pylori (Pu4 vs P12). The activity of the oligosaccharide mimetics is speculated to be due to the GlcNAc residues being able to adopt spatial arrangements accessible to the anti H. pylori hexasaccharide which may be important for activity. (C) 2012 Elsevier Ltd. All rights reserved.