3β-D-glucopyranosyl-ethinylestradiol | 55093-92-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-D-glucopyranosyl-ethinylestradiol
• CAS: 55093-92-0
• 化学式: C₂₆H₃₄O₇
• 分子量: 458.552
• InChiKey: PPANCHFCINNDOC-LMFIQQKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  119.61
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 炔雌醇 、 alkaline earth salt of/the/ methylsulfuric acid 以 水 、 丙酮 为溶剂， 反应 24.0h， 以74%的产率得到3β-D-glucopyranosyl-ethinylestradiol
  参考文献：
  名称：

  Efficiently regioselective glucosylation of estrogen analogues mediated by fungus Rhizopus oryzae AS 3.2380

  摘要：

  Compared with estrogens, estrogen 3 beta-glucosides display more superiority in uptake and metabolism, which are thought to be potential replacement therapy agents for female. In the present research, various estrogen 3 beta-glucosides (1a-6a) were obtained using the biotransformation experiment of estrogen substrates mediated by Rhizopus oryzae AS 3.2380. The characteristics of estrogens glucosylation with high specificity and regioselectivity were observed. An optimal incubation medium was determined as the pH 7.0 (sodium phosphate buffer), 20 g/L (D-glucose) and 24 h incubation time with the yields > 70%. A environment friendly preparative method for these glucosides was also established using MCI (Middle chromatogram isolated gel) column chromatography eluted with ethanol aqueous, which could give estrogen 3 beta-glucosides with the purity > 95%. This study suggested that R. oryzae AS 3.2380 could be an efficient engineering bacteria for the glucosylation of chemical substance. Glucosyltransferase also could be prepared from R. oryzae AS 3.2380.

  DOI：

  10.1016/j.catcom.2017.04.027

文献信息

• Efficiently regioselective glucosylation of estrogen analogues mediated by fungus Rhizopus oryzae AS 3.2380
  作者：Ping Li、Chengpeng Sun、Yan Wang、Shumei Wang、Chunyan Yan、Sa Deng、Xiaokui Huo、Lei Feng、Chao Wang、Yan Tian、Baojing Zhang、Xiaochi Ma

  DOI：10.1016/j.catcom.2017.04.027

  日期：2017.7

  Compared with estrogens, estrogen 3 beta-glucosides display more superiority in uptake and metabolism, which are thought to be potential replacement therapy agents for female. In the present research, various estrogen 3 beta-glucosides (1a-6a) were obtained using the biotransformation experiment of estrogen substrates mediated by Rhizopus oryzae AS 3.2380. The characteristics of estrogens glucosylation with high specificity and regioselectivity were observed. An optimal incubation medium was determined as the pH 7.0 (sodium phosphate buffer), 20 g/L (D-glucose) and 24 h incubation time with the yields > 70%. A environment friendly preparative method for these glucosides was also established using MCI (Middle chromatogram isolated gel) column chromatography eluted with ethanol aqueous, which could give estrogen 3 beta-glucosides with the purity > 95%. This study suggested that R. oryzae AS 3.2380 could be an efficient engineering bacteria for the glucosylation of chemical substance. Glucosyltransferase also could be prepared from R. oryzae AS 3.2380.