esculetin-7-O-α-D-glucoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: esculetin-7-O-α-D-glucoside
• 英文别名: 6-hydroxy-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• 化学式: C₁₅H₁₆O₉
• 分子量: 340.287
• InChiKey: WNBCMONIPIJTSB-LFHLZQBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6,7-二羟基香豆素 、 蔗糖 在 sodium acetate 、 L_. citreum DSM 5577 glucansucrase 、 calcium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 aesculin 、 esculetin-7-O-α-D-glucoside
  参考文献：
  名称：

  Glucansucrases from lactic acid bacteria as biocatalysts for multi-ring catechol glucosylation

  摘要：

  Catechins are the major group of bioactive flavanols in green tea and cacao. 17 glucansucrase-active strains were identified from a set of 41 lactic acid bacteria, which were able to glucosylate (+)-catechin in a non-natural acceptor reaction. In total cell free extracts of 12Leuconostocand 5Weissellastrains were active on catechin and also 8 cell fractions exhibited catechin glucosylation activity. Six enzymes were selected for further evaluation and enriched up to 37 fold in yields of at least 40%. Glucansucrase ofL. citreumDSM 5577 was the most efficient biocatalyst for (+)-catechin transformation with conversions of >40% after 24 h. NMR analysis of the major reaction product confirmed the (+)-catechin-4 '-O-alpha-d-glucoside. OnlyL. kimchiB-65337 produced a second catechin monoglucoside. Four out of six glucansucrases glucosylated esculetin and all enzymes were active on haematoxylin. Glucansucrases ofL. citreumDSM 5577,L. kimchiB-65337 andW. beninensisDSM 22752 were the best suited biocatalysts with conversions of >30% for esculetin and >60% for haematoxylin.W. beninensisDSM 22752 glucansucrase produced 89% haematoxylin glucosides without process optimization.L. kimchiB-65337 andW. beninensisDSM 22752 synthesized >40% diglucosides with the bifunctional haematoxylin. NMR analysis of the purified esculetin products confirmed formation of the 6-O-alpha-d- and 7-O-alpha-d-glucosides. Also two haematoxylin monoglucosides were identified as the 9-O-alpha-d- and 3-O-alpha-d-glucosides.

  DOI：

  10.1080/10242422.2020.1784882

文献信息

• Glucansucrases from lactic acid bacteria as biocatalysts for multi-ring catechol glucosylation
  作者：Johannes Nolte、Alexander Kempa、Matthias Hochgürtel、Ulrich Schörken

  DOI：10.1080/10242422.2020.1784882

  日期：2021.1.2

  Catechins are the major group of bioactive flavanols in green tea and cacao. 17 glucansucrase-active strains were identified from a set of 41 lactic acid bacteria, which were able to glucosylate (+)-catechin in a non-natural acceptor reaction. In total cell free extracts of 12Leuconostocand 5Weissellastrains were active on catechin and also 8 cell fractions exhibited catechin glucosylation activity. Six enzymes were selected for further evaluation and enriched up to 37 fold in yields of at least 40%. Glucansucrase ofL. citreumDSM 5577 was the most efficient biocatalyst for (+)-catechin transformation with conversions of >40% after 24 h. NMR analysis of the major reaction product confirmed the (+)-catechin-4 '-O-alpha-d-glucoside. OnlyL. kimchiB-65337 produced a second catechin monoglucoside. Four out of six glucansucrases glucosylated esculetin and all enzymes were active on haematoxylin. Glucansucrases ofL. citreumDSM 5577,L. kimchiB-65337 andW. beninensisDSM 22752 were the best suited biocatalysts with conversions of >30% for esculetin and >60% for haematoxylin.W. beninensisDSM 22752 glucansucrase produced 89% haematoxylin glucosides without process optimization.L. kimchiB-65337 andW. beninensisDSM 22752 synthesized >40% diglucosides with the bifunctional haematoxylin. NMR analysis of the purified esculetin products confirmed formation of the 6-O-alpha-d- and 7-O-alpha-d-glucosides. Also two haematoxylin monoglucosides were identified as the 9-O-alpha-d- and 3-O-alpha-d-glucosides.