4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside | 566199-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-3-[(4-methoxyphenyl)methoxy]-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 566199-66-4
• 化学式: C₄₂H₄₄O₆S
• 分子量: 676.874
• InChiKey: BPLZCHUQKKZVKY-WZYMAVNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， -55.0~20.0 ℃ 、100.0 kPa 条件下， 反应 6.17h， 生成 4-methoxyphenyl 2-O-methoxymethyl-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：

  4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-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

文献信息

• A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins
  作者：Jörgen Ohlsson、Ulf J. Nilsson

  DOI：10.1016/s0040-4039(03)00475-1

  日期：2003.3

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.