2-naphthyl 2,3-di-O-benzoyl-β-D-xylopyranoside | 174193-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 2,3-di-O-benzoyl-β-D-xylopyranoside
• CAS: 174193-91-0
• 化学式: C₂₉H₂₄O₇
• 分子量: 484.505
• InChiKey: BLQYLXFCUSNYLY-KGWIZABPSA-N

反应信息

• 作为反应物：
  描述：

  2-naphthyl 2,3-di-O-benzoyl-β-D-xylopyranoside 在 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.67h， 生成 2-naphthyl O-(β-D-galactopyranosyl)-(1<*>4)-β-D-xylopyranoside
  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：

  在 吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 生成 2-naphthyl 2,3-di-O-benzoyl-β-D-xylopyranoside
  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