benzyl 2,3-di-O-(β-D-galactopyranosyl)-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-di-O-(β-D-galactopyranosyl)-β-D-galactopyranoside
• 英文别名: Gal(b1-2)[Gal(b1-3)]Gal(b)-O-Bn；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₅H₃₈O₁₆
• 分子量: 594.567
• InChiKey: BEDWWZCYHCGAKV-DGWZPVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-di-O-(β-D-galactopyranosyl)-β-D-galactopyranoside 、 3'-sialyllactose 在 Tris buffer 、 Trypanosoma cruzi trans-sialidase 、 sodium chloride 作用下， 反应 3.0h， 以7 mg的产率得到benzyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-[β-D-galactopyranosyl-(1->2)]-β-D-galactopyranoside
  参考文献：
  名称：

  Selective sialylation of 2,3-di-O-(β-d-galactopyranosyl)-d-galactose catalyzed by Trypanosoma cruzi trans-sialidase

  摘要：

  Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal beta-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-( beta-D-galactopyranosyl)-D-galactose 1 is an external unit in the larger oligosaccharides of the mucins and a site for sialylation. The trisaccharide was previously synthesized in our laboratory. The last step of the synthesis was the hydrogenolysis of the crystalline benzyl trisaccharide. Herein we prove that the trisaccharide 1, its alditol 3 and the benzyl glycoside 2 are good acceptors of sialic acid and effective inhibitors of the sialylation of N-acetyllactosamine catalyzed by TcTS. Furthermore, selective sialylation of the 1 3 linked galactopyranose in glycoside 2 was determined by one and two-dimensional NMR analysis. In contrast, the flexible 2,3-di-O-(beta-D-galactopyranosyl)-D-galactitol 3 is sialylated in either one of the two possible sites. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.075

文献信息

• Selective sialylation of 2,3-di-O-(β-d-galactopyranosyl)-d-galactose catalyzed by Trypanosoma cruzi trans-sialidase
  作者：Rosalía Agusti、Verónica M. Mendoza、Carola Gallo-Rodriguez、Rosa M. de Lederkremer

  DOI：10.1016/j.tetasy.2004.11.075

  日期：2005.1

  Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal beta-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-( beta-D-galactopyranosyl)-D-galactose 1 is an external unit in the larger oligosaccharides of the mucins and a site for sialylation. The trisaccharide was previously synthesized in our laboratory. The last step of the synthesis was the hydrogenolysis of the crystalline benzyl trisaccharide. Herein we prove that the trisaccharide 1, its alditol 3 and the benzyl glycoside 2 are good acceptors of sialic acid and effective inhibitors of the sialylation of N-acetyllactosamine catalyzed by TcTS. Furthermore, selective sialylation of the 1 3 linked galactopyranose in glycoside 2 was determined by one and two-dimensional NMR analysis. In contrast, the flexible 2,3-di-O-(beta-D-galactopyranosyl)-D-galactitol 3 is sialylated in either one of the two possible sites. (C) 2004 Elsevier Ltd. All rights reserved.