methyl gallate 3-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl gallate 3-O-β-D-glucopyranoside
• 英文别名: methyl gallyl 3-O-α-D-glucopyranoside
• 化学式: C₁₄H₁₈O₁₀
• 分子量: 346.291
• InChiKey: HVFHEQBFSAYLMY-CGUBKOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166.14
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  没食子酸甲酯 、 蔗糖 在 3-吗啉丙磺酸 、 recombinant sucrose phosphorylase from Thermoanaerobacterium thermosaccharolyticum, mutant R₁₃₄A 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 以35.3%的产率得到methyl gallate 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization

  摘要：

  Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.

  DOI：

  10.1021/acs.jafc.5b04380

文献信息

• Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization
  作者：Karel De Winter、Griet Dewitte、Mareike E. Dirks-Hofmeister、Sylvie De Laet、Helena Pelantová、Vladimír Křen、Tom Desmet

  DOI：10.1021/acs.jafc.5b04380

  日期：2015.11.25

  Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.