α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranose
• 英文别名: fabatriose；α-L-rhamnopyranosyl (1->2)-β-D-galactopyranosyl (1->2)-D-glucuronopyranoside；(2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4,6-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₈H₃₀O₁₆
• 分子量: 502.427
• InChiKey: NDHWVPLSWYRBNC-ULFDKFODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranose 以 甲醇 、 乙醚 为溶剂， 生成 (2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4,6-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemical transglycosylation of functional bioactive glyco-linkages

  摘要：

  The natural functional bioactive oligosaccharides moieties, mimosatetraose and fabatriose, were cut off from julibrosides and soyasaponin I by chemical and enzymatic methods, respectively, and were pasted to diosgenin to give neosaponins 1 and 2. The obtained neosaponins were tested for cytotoxicity and hepatoprotective activity. This method could be applied to the synthesis of novel bioactive glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00519-x
• 作为产物：
  描述：

  大豆皂苷 Bb 在 glycyrrhizinic acid hydrolase 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 生成 α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranose
  参考文献：
  名称：

  Chemical transglycosylation of functional bioactive glyco-linkages

  摘要：

  The natural functional bioactive oligosaccharides moieties, mimosatetraose and fabatriose, were cut off from julibrosides and soyasaponin I by chemical and enzymatic methods, respectively, and were pasted to diosgenin to give neosaponins 1 and 2. The obtained neosaponins were tested for cytotoxicity and hepatoprotective activity. This method could be applied to the synthesis of novel bioactive glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00519-x

文献信息

• Synthesis of Neosaponins Carrying Oligosaccharides from Natural Products
  作者：Toshihiro Nohara、Tsuyoshi Ikeda、Junei Kinjo、Tetsuya Kajimoto

  DOI：10.3987/com-99-8612

  日期：——
• Purification and Some Properties of Soybean Saponin Hydrolase from<i>Aspergillus oryzae</i>KO-2
  作者：Shigemitsu Kudou、Iwao Tsuizaki、Teiji Uchida、Kazuyoshi Okubo

  DOI：10.1080/00021369.1991.10870531

  日期：1991.1

  We had investigated the enzymatic hydrolysis of soybean saponins and selected soybean saponin hydrolase from Aspergillus oryzae KO-2. We attempted purification of this enzyme for further characterization. This enzyme was purified 1500-fold using ammonium sulfate fractionation and Sephadex G-200 gel filtrations. The enzyme was electrophoretically homogeneous and a glycoprotein by PAS staining. By gel filtration, the molecular weight of enzyme was 158,000 and SDS-PAGE showed the enzyme to have a tetrameric structure composed of heterogeneous subunits of 35,000 and 45,000 The enzyme activity was stable at temperatures below 40°C and stable from pH 5.0 to 8.0. The optimum pH was pH 4.5 to 5.0 and the optimum temperature was 50°C. The Km and Vmax for soyasaponin I were 0.48 mm and 9.8 μmol/hr mg protein, respectively. After hydrolysis with the enzyme, soyasapogenol B and α-l-rhamnopyranosyl (1 → 2)-β-d-galactopyranosyl (1 → 2)-d-glucuronopyrano-side were released from soyasaponin I.