(-)-epicatechin-3'-O-α-D-glucopyranoside | 251340-45-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-epicatechin-3'-O-α-D-glucopyranoside
• 英文别名: 3'-O-α-D-glucopyranosyl epicatechin
• CAS: 251340-45-1
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: ZZTOVZGFHZQEAT-CWKWDLCCSA-N

物化性质

• 沸点：
  824.0±65.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  189.53
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (-)-epicatechin-3'-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2.9%的产率得到3'-O-α-D-cellobiopyranosyl epicatechin
  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：

  蔗糖 、 表儿茶素 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58.1%的产率得到(-)-epicatechin-3'-O-α-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

• Redesign of the Active Site of Sucrose Phosphorylase through a Clash-Induced Cascade of Loop Shifts
  作者：Michael Kraus、Clemens Grimm、Jürgen Seibel

  DOI：10.1002/cbic.201500514

  日期：2016.1

  Repositioning key loops by adding a clash‐inducing hydrophobic Phe—remodelling a sucrose phosphorylase into a polyphenol transglucosidase: Introducing a sterically demanding residue into the active site of a sucrose phosphorylase enlarged the active site through indirect effects arising from a cascade of conformational changes. Aromatic acceptors could thus be glucosylated.

  通过添加诱导冲突的疏水性Phe来重新定位关键环，从而将蔗糖磷酸化酶重塑为多酚转葡糖苷酶：将空间需求的残基引入蔗糖磷酸化酶的活性位点通过一系列构象变化产生的间接作用扩大了活性位点。芳香受体因此可以被糖基化。
• Synthesis of epicatechin glucosides by a β-cyclodextrin glycosyltransferase
  作者：Pornpun Aramsangtienchai、Warinthorn Chavasiri、Kazuo Ito、Piamsook Pongsawasdi

  DOI：10.1016/j.molcatb.2011.07.013

  日期：2011.12

  Enzymatic synthesis of (-)-epicatechin (EC) glucosides was performed through the transglucosylation reaction catalyzed by the cyclodextrin glycosyltransferase (CGTase) from Paenibacillus sp. RB01. The enzyme showed the same product specificity for the three donor substrates, starch, beta-cyclodextrin and maltoheptaose (G7). Using beta-cyclodextrin as the glucosyl donor. several EC glucoside products were obtained at an overall minimal yield of 18.1%. The structures of the four main products were elucidated by MS and NMR techniques as (-)-EC-3'-O-alpha-D-glucopyranoside (EC3A), (-)-EC-3'-O-alpha-D-diglucopyranoside (EC3B), (-)-EC-3'-O-alpha-D-triglucopyranoside (EC3C) and (-)-EC-4'-O-alpha-D-glucopyranoside (EC4A). Of these, EC3A was the major product while EC4A, unique for this CGTase, was formed in the lowest amount. The water solubility and stability against UV irradiation of EC3A were significantly higher than that of EC. Although the antioxidant activity was 1.5-fold lower, the advantage of the enhanced solubility and stability makes the EC3A glucoside more beneficial as food ingredient than its parent EC. (C) 2011 Elsevier B.V. All rights reserved.