ethyl gallyl 4-O-α-D-glucopyranoside | 1569303-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl gallyl 4-O-α-D-glucopyranoside
• 英文别名: ethyl 3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• CAS: 1569303-42-9
• 化学式: C₁₅H₂₀O₁₀
• 分子量: 360.318
• InChiKey: DACGOUXXKWQWLE-BJIWRROBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl gallyl 4-O-α-D-glucopyranoside 、 对氟苯甲醇 在 recombinant cellodextrin phosphorylase from Clostridium stercocarium 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以8.3%的产率得到ethyl gallyl 4-O-α-D-cellobiopyranoside
  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
• 作为产物：
  描述：

  没食子酸乙酯 、 蔗糖 在 hecombinant sucrose phosphorylase from Bifidobacterium adolescentis 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以1.83 g的产率得到ethyl gallyl 4-O-α-D-glucopyranoside
  参考文献：
  名称：

  二糖磷酸化酶的双相催化：使用蔗糖磷酸化酶的化学酶法合成α-d-葡糖苷

  摘要：

  由于其广泛的受体特异性，蔗糖磷酸化酶（SP）已被用于将葡萄糖转移至多种受体分子。不幸的是，SP对这些受体的亲和力低（K m > 1 M）通常促使添加助溶剂，助溶剂通常不能溶解足够的底物或逐渐引起酶抑制和变性。在这项工作中，确定缓冲液/乙酸乙酯的比例为5：3是最佳溶剂系统，从而允许在双相系统中使用SP。的反应条件的仔细优化启用的范围α-的合成d -glucosides，如肉桂α- d吡喃葡萄糖苷，香叶基α- d吡喃葡萄糖苷，2- ö-α- d吡喃葡萄糖基邻苯三酚，和烷基gallyl 4-系列ö -α- d -glucopyranosides。通过在辅助溶剂和双相反应系统中比较邻苯三酚的葡萄糖基化进一步说明了双相催化的有用性。前者的受体收率仅达到17.4％，而使用双相催化时，大约60％的初始邻苯三酚会转化。

  DOI：

  10.1021/op400302b

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.
• Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of α-<scp>d</scp>-Glucosides Using Sucrose Phosphorylase
  作者：Karel De Winter、Tom Desmet、Tim Devlamynck、Lisa Van Renterghem、Tom Verhaeghe、Helena Pelantová、Vladimír Křen、Wim Soetaert

  DOI：10.1021/op400302b

  日期：2014.6.20

  this work, a buffer/ethyl acetate ratio of 5:3 was identified to be the optimal solvent system, allowing the use of SP in biphasic systems. Careful optimization of the reaction conditions enabled the synthesis of a range of α-d-glucosides, such as cinnamyl α-d-glucopyranoside, geranyl α-d-glucopyranoside, 2-O-α-d-glucopyranosyl pyrogallol, and series of alkyl gallyl 4-O-α-d-glucopyranosides. The usefulness

  由于其广泛的受体特异性，蔗糖磷酸化酶（SP）已被用于将葡萄糖转移至多种受体分子。不幸的是，SP对这些受体的亲和力低（K m > 1 M）通常促使添加助溶剂，助溶剂通常不能溶解足够的底物或逐渐引起酶抑制和变性。在这项工作中，确定缓冲液/乙酸乙酯的比例为5：3是最佳溶剂系统，从而允许在双相系统中使用SP。的反应条件的仔细优化启用的范围α-的合成d -glucosides，如肉桂α- d吡喃葡萄糖苷，香叶基α- d吡喃葡萄糖苷，2- ö-α- d吡喃葡萄糖基邻苯三酚，和烷基gallyl 4-系列ö -α- d -glucopyranosides。通过在辅助溶剂和双相反应系统中比较邻苯三酚的葡萄糖基化进一步说明了双相催化的有用性。前者的受体收率仅达到17.4％，而使用双相催化时，大约60％的初始邻苯三酚会转化。