O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose | 174193-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose
• CAS: 174193-94-3
• 化学式: C₄₃H₄₄O₁₉
• 分子量: 864.811
• InChiKey: ZJQUMOMHZNZLRO-ZPCCSOMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 2-naphthyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and glycosaminoglycan priming activity of three disaccharides related to the linkage region tetrasaccharide of proteoglycans

  摘要：

  To test if disaccharides might serve as primers of oligosaccharide synthesis in animal cells, we synthesized 2-naphthyl O-(beta-D-galactopyranosyl)-(1-->4)-beta-D-xylopyranoside, 2-naphthyl O-(beta-D-galactopyranosyl)-(1 -->3)-beta-D-galactopyranoside, and 2-naphthyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-beta-D-galactopyranoside. These three disaccharides are related to subunits of the linkage tetrasaccharide of heparan sulfate and chondroitin sulfate chains in animal cell proteoglycans. The disaccharides were synthesized with coupling efficiencies of 40-70% using thioglycosides or by activating the monosaccharides with trichloroacetimidate. The structures of these compounds were confirmed by H-1 NMR, C-13 NMR and elemental analysis. The ability of these disaccharides to prime glycosaminoglycan chains was examined in a Chinese hamster ovary cell mutant, pgsA 745, which lacks xylosyltransferase. The missing enzyme renders the cells dependent on exogenous primers for making glycosaminoglycan chains. 2-Naphthyl O-(beta-D-galactopyranosyl)-(1-->3)-beta-D-galactopyranoside and 2-naphthyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-beta-D-galactopyranoside did not stimulate glycosaminoglycan synthesis, but 2-naphthyl O-(beta-D-galactopyranosyl)-(1-->4)-beta-D-xylopyranoside at high concentration primed chains. The peracetylated derivative (2-naphthyl O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)2,3-di-O-acetyl-beta-D-xylopyranoside) primed chains at lower concentration (100 mu M), suggesting that cells took up the compound and removed the acetyl groups apparently in the compartment where glycosaminoglycan synthesis occurs.

  DOI：

  10.1016/0008-6215(95)00304-5
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 、 1-O-acetyl-2,4,6-tri-O-benzoyl-1β-D-galactopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis and glycosaminoglycan priming activity of three disaccharides related to the linkage region tetrasaccharide of proteoglycans

  摘要：

  To test if disaccharides might serve as primers of oligosaccharide synthesis in animal cells, we synthesized 2-naphthyl O-(beta-D-galactopyranosyl)-(1-->4)-beta-D-xylopyranoside, 2-naphthyl O-(beta-D-galactopyranosyl)-(1 -->3)-beta-D-galactopyranoside, and 2-naphthyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-beta-D-galactopyranoside. These three disaccharides are related to subunits of the linkage tetrasaccharide of heparan sulfate and chondroitin sulfate chains in animal cell proteoglycans. The disaccharides were synthesized with coupling efficiencies of 40-70% using thioglycosides or by activating the monosaccharides with trichloroacetimidate. The structures of these compounds were confirmed by H-1 NMR, C-13 NMR and elemental analysis. The ability of these disaccharides to prime glycosaminoglycan chains was examined in a Chinese hamster ovary cell mutant, pgsA 745, which lacks xylosyltransferase. The missing enzyme renders the cells dependent on exogenous primers for making glycosaminoglycan chains. 2-Naphthyl O-(beta-D-galactopyranosyl)-(1-->3)-beta-D-galactopyranoside and 2-naphthyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-beta-D-galactopyranoside did not stimulate glycosaminoglycan synthesis, but 2-naphthyl O-(beta-D-galactopyranosyl)-(1-->4)-beta-D-xylopyranoside at high concentration primed chains. The peracetylated derivative (2-naphthyl O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)2,3-di-O-acetyl-beta-D-xylopyranoside) primed chains at lower concentration (100 mu M), suggesting that cells took up the compound and removed the acetyl groups apparently in the compartment where glycosaminoglycan synthesis occurs.

  DOI：

  10.1016/0008-6215(95)00304-5