zearalanone 4-O-β-D-glucuronide | 1032558-37-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: zearalanone 4-O-β-D-glucuronide
• 英文别名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(4S)-18-hydroxy-4-methyl-2,8-dioxo-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-16-yl]oxy]oxane-2-carboxylic acid
• CAS: 1032558-37-4
• 化学式: C₂₄H₃₂O₁₁
• 分子量: 496.511
• InChiKey: CNYMGRCJMAJKPT-DAEVSXOKSA-N

物化性质

• 沸点：
  842.2±65.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  180
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  uridine 5'-diphosphoglucuronic acid 、 玉米烯酮 在 uridine 5'-diphosphoglucuronyl transferase 、 calcium chloride 、 1,4-二巯基-2,3-丁二醇 、 bovine serum albumin 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到zearalanone 4-O-β-D-glucuronide
  参考文献：
  名称：

  Preparative Enzymatic Synthesis of Glucuronides of Zearalenone and Five of Its Metabolites

  摘要：

  The resorcylic acid lactones zearalenone (1), alpha-zearalenol (2), beta-zearalenol (3), alpha-zearalanol (zeranol) (4), beta-zearalanol (taleranol) (5), and zearalanone (6) were converted to their glucuronides on a preparative scale in good yields. Reactions were conducted with bovine uridine 5'-diphosphoglucuronyl transferase (UDPGT) as catalyst and uridine 5'-diphosphoglucuronic acid (UDPGA) as cofactor. The glucuronides were isolated by column chromatography and characterized by NMR spectroscopy and mass spectrometry. Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6'-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated. In the case of 3, the 2-O-glucuronide was isolated as the minor product. Overall isolated yields of glucuronides, performed on a 20-50 mg scale, were typically ca. 80%. based on, the resorcylic acid lactone starting material. LC-UV-MS(2) analysis of purified specimens revealed MS(2) fragmentations useful for defining the point of attachment of the glucuronide moiety to the zearalenone nucleus.

  DOI：

  10.1021/jf800379z

文献信息

• Preparative Enzymatic Synthesis of Glucuronides of Zearalenone and Five of Its Metabolites
  作者：David E. Stevenson、Richard P. Hansen、Jared I. Loader、Dwayne J. Jensen、Janine M. Cooney、Alistair L. Wilkins、Christopher O. Miles

  DOI：10.1021/jf800379z

  日期：2008.6.1

  The resorcylic acid lactones zearalenone (1), alpha-zearalenol (2), beta-zearalenol (3), alpha-zearalanol (zeranol) (4), beta-zearalanol (taleranol) (5), and zearalanone (6) were converted to their glucuronides on a preparative scale in good yields. Reactions were conducted with bovine uridine 5'-diphosphoglucuronyl transferase (UDPGT) as catalyst and uridine 5'-diphosphoglucuronic acid (UDPGA) as cofactor. The glucuronides were isolated by column chromatography and characterized by NMR spectroscopy and mass spectrometry. Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6'-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated. In the case of 3, the 2-O-glucuronide was isolated as the minor product. Overall isolated yields of glucuronides, performed on a 20-50 mg scale, were typically ca. 80%. based on, the resorcylic acid lactone starting material. LC-UV-MS(2) analysis of purified specimens revealed MS(2) fragmentations useful for defining the point of attachment of the glucuronide moiety to the zearalenone nucleus.