4-methylphenyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside | 592527-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
• 英文别名: 4-methylphenyl 2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside
• CAS: 592527-55-4
• 化学式: C₂₁H₂₆O₆S
• 分子量: 406.5
• InChiKey: OSAYYSNNBIYNOK-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 、 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， 反应 6.17h， 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
• 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 6.0h， 生成 4-methylphenyl 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

• Synthesis of Oligosaccharides Containing the <i>S</i>-Gal<i>p</i>(α1 → 3)Gal<i>p</i> Unit, Glycomimetic of the Epitope Recognized by Lytic Antibodies
  作者：Pablo Morrone-Pozzuto、María Laura Uhrig、Rosalia Agusti

  DOI：10.1021/acs.joc.2c01059

  日期：2022.10.21

  Two important activities take place in the surface of Trypanosoma cruzi, the agent of Chagas disease: the trans-sialidase (TcTS) catalyzes the transfer of sialic acid from the host glycoconjugates to the mucin-like glycoproteins from the parasite and the presence of lytic antibodies recognize the epitope α-Galp(1 → 3)-β-Galp(1 → 4)-α-GlcNAcp. This antigenic structure is known to be present in the parasite

  克氏锥虫（恰加斯病的病原体）的表面发生两项重要活动：转唾液酸酶 (TcTS) 催化唾液酸从宿主糖缀合物转移到寄生虫的粘蛋白样糖蛋白，以及裂解抗体的存在识别表位 α-Gal p (1 → 3)-β-Gal p (1 → 4)-α-GlcNAc p。已知这种抗原结构存在于寄生虫粘蛋白中；然而，为了成为转唾液酸酶的底物，一些半乳糖残基应该位于 β-Gal p配置。要研究这两种活动之间的相互作用，重要的是要计算合成结构以及结构相关的糖模拟物。为此，我们解决了含有 1 - S -α-Gal p (1 → 3)-β-Gal p基序的三糖和两个异构四糖的合成，这是裂解抗体识别的表位的硫类似物。从常见的乳糖前体开始，通过使用不同的活化供体进一步糖基化的半乳糖残基构型的双重反转来合并硫功能。通过高效阴离子交换色谱法测定，在 TcTS 催化的反应中，两种四糖都是唾液酸的良好受体。