| 1356547-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1356547-38-0
• 化学式: C₂₇H₄₄N₈O₁₄
• 分子量: 704.692
• InChiKey: FACURNFMLFINNJ-ZRMGYUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.09
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  332.37
• 氢给体数：
  10.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 以96 mg的产率得到
  参考文献：
  名称：

  Diazo Transfer and Click Chemistry in the Solid Phase Syntheses of Lysine-Based Glycodendrimers as Antagonists against Escherichia coli FimH

  摘要：

  Uropathogenic Escherichia coli infections, ultimately leading to cystitis and pyelonephritis, are initially mediated by the adhesion of the bacterial FimH to the transmembrane glycoprotein uroplakin-1a present at the surface of urothelial cells. The adhesion is based on the recognition and high avidity binding between the high-mannose glycans of the uroplakin and the FimH, a man nose-specific lectin located at the tip of type 1 fimbriae. We found that synthetic multiantennary mannopyranosides glycodendrons, harboring triazole functionality at the anomeric position, were potent hemagglutination inhibitors of guinea pig erythrocytes and E. coli. A mannosylated dendrimer exposing up to sixteen sugar residues showed an HAI titer of 1 mu M and was thus 500-fold more potent than the corresponding monovalent methyl alpha-D-mannopyranoside. The synthesis of the glycodendrons involved highly efficient solid-phase synthesis of branched L-lysine scaffolds, diazo transfer reaction on the terminal amine residues, and 1,3-dipolar copper-catalyzed azide-alkyne cycloaddition using propargyl alpha-D-mannopyranoside.

  DOI：

  10.1021/mp200490b