1-O-α-D-cellobiopyranosyl hydroquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-α-D-cellobiopyranosyl hydroquinone
• 英文别名: Glc(b1-4)Glc(a)-O-Ph(4-OH)；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₂₆O₁₂
• 分子量: 434.397
• InChiKey: UPQIJOKWUQETKU-BYKNIKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  对苯二酚 、 蔗糖 在 3-吗啉丙磺酸 、 recombinant cellodextrin phosphorylase from Clostridium stercocarium 、 recombinant sucrose phosphorylase from Bifidobacterium adolescentis 作用下， 以 乙酸乙酯 为溶剂， 反应 96.0h， 生成 1-O-α-D-cellobiopyranosyl hydroquinone
  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.