4-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside | 592527-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
• CAS: 592527-60-1
• 化学式: C₆₁H₆₄O₁₂
• 分子量: 989.172
• InChiKey: LJGNCHGOUCTORA-NYCUWDHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.05
• 重原子数：
  73.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 2.0h， 生成 4-methoxyphenyl 2-O-propyl-α-D-galactopyranosyl-(1->4)-β-galactopyranoside
  参考文献：
  名称：

  Quantitative studies of the binding of the class II PapG adhesin from uropathogenic Escherichia coli to oligosaccharides

  摘要：

  Binding of the class 11 PapG adhesin, found at the tip of filamentous pili on Escherichia coli, to the carbohydrate moiety of globoseries glycolipids in the human kidney is a key step in development of pyelonephritis, a severe form of urinary tract infection. An assay based on surface plasmon resonance for quantification of the binding of the class 11 PapG adhesin to oligosaccharides has been developed. Using this assay dissociation constants ranging from 80 to 540 muM were determined for binding of the PapG adhesin to di-pentasaccharide fragments from the globoseries of glycolipids. A series of galabiose derivatives, modified at the anomeric position, O-2' or O-3', was also investigated. The anomeric position appeared to be the most promising for development of improved inhibitors of PapG-mediated adhesion of E. coli. p-Methoxyphenyl galabioside was found to be most potent (K-d = 140 muM), and binds to PapG almost as well as the Forssman pentasaccharide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00114-7
• 作为产物：
  描述：

  (2S,3R,4R,5R,6R)-5-[(2R,3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3,4-diol 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 4-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Quantitative studies of the binding of the class II PapG adhesin from uropathogenic Escherichia coli to oligosaccharides

  摘要：

  Binding of the class 11 PapG adhesin, found at the tip of filamentous pili on Escherichia coli, to the carbohydrate moiety of globoseries glycolipids in the human kidney is a key step in development of pyelonephritis, a severe form of urinary tract infection. An assay based on surface plasmon resonance for quantification of the binding of the class 11 PapG adhesin to oligosaccharides has been developed. Using this assay dissociation constants ranging from 80 to 540 muM were determined for binding of the PapG adhesin to di-pentasaccharide fragments from the globoseries of glycolipids. A series of galabiose derivatives, modified at the anomeric position, O-2' or O-3', was also investigated. The anomeric position appeared to be the most promising for development of improved inhibitors of PapG-mediated adhesion of E. coli. p-Methoxyphenyl galabioside was found to be most potent (K-d = 140 muM), and binds to PapG almost as well as the Forssman pentasaccharide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00114-7