(-)-epicatechin-4'-O-α-D-glucopyranoside | 183387-70-4

• 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-4'-O-α-D-glucopyranoside
• CAS: 183387-70-4
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: LTDLFQZRSXJVAN-CWKWDLCCSA-N

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

• 作为产物：
  描述：

  麦芽七糖 、 表儿茶素 在 β-cyclodextrin glycosyltransferase-containing Paenibacillus sp. RB01 culture broth 作用下， 反应 24.0h， 生成 (-)-epicatechin-3'-O-α-D-glucopyranoside 、 (-)-epicatechin-4'-O-α-D-glucopyranoside 、 (2R,3R)-2-(3-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxyphenyl)chromane-3,5,7-triol 、
  参考文献：
  名称：

  Synthesis of epicatechin glucosides by a β-cyclodextrin glycosyltransferase

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2011.07.013