4-O-{3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-1,2,3,6-tetrakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose | 99877-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4-O-{3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-1,2,3,6-tetrakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose
• 英文别名: 4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose；4-O-digalloyl-1,2,3,6-tetra-O-beta-D-galloylglucose；[(2R,3R,4S,5R,6S)-3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 99877-83-5
• 化学式: C₄₈H₃₆O₃₀
• 分子量: 1092.8
• InChiKey: UZGMNWZQVBQIPC-YHNAUUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  511
• 氢给体数：
  17
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  4-O-{3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-1,2,3,6-tetrakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose 、 1-没食子酸酰葡萄糖 在 beta-glucogallin O-galloyltransferase citrate buffer 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2,4-O-digalloyl-1,3,6-tri-O-beta-D-galloylglucose
  参考文献：
  名称：

  Gallotannin biosynthesis: purification of β -glucogallin: 1,2,3,4,6-pentagalloyl- β -d-glucose galloyltransferase from sumac leaves fn1 fn1In honour of Professor G. H. Neil Towers’ 75th birthday.

  摘要：

  An enzyme from leaves of staghorn sumac (Rhus typhina) that catalysed the galloylation of 1,2,3,4, 6-penta-O-galloyl-beta-D-glucose to the gallotannin, 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-beta-D-glucose, was purified more than 500-fold to apparent homogeneity. beta-Glucogallin (1-O-galloyl-beta-D-glucopyranose) served as activated acyl donor in this conversion. For the native enzyme, a M(r) value of 170,000 was determined by gel filtration, while a single polypeptide band of M(r) 42,000 was detected by SDS-PAGE. The acyltransferase had pH and temperature optima of 4-4.5 and 25 degrees, respectively, and was most stable between pH 3 and 4.5. Besides the major substrate, pentagalloylglucose, also 1,2,3,6-tetragalloylglucose and hexa- to nona-substituted gallotannins were accepted as minor substrates by this new enzyme for which the systematic name "beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose (3-O-galloyl)-galloyltransferase" (EC 2.3.1.-) is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00014-4
• 作为产物：
  描述：

  1,2,3,4,6-O-五没食子酰葡萄糖 、 1-没食子酸酰葡萄糖 在 beta-glucogallin O-galloyltransferase citrate buffer 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-O-{3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-1,2,3,6-tetrakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose 、 2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose 、 hexagalloyl β-D-glucose 、 3-O-trigalloyl-1,2,4,6-tetra-O-beta-D-galloylglucose
  参考文献：
  名称：

  Gallotannin biosynthesis: purification of β -glucogallin: 1,2,3,4,6-pentagalloyl- β -d-glucose galloyltransferase from sumac leaves fn1 fn1In honour of Professor G. H. Neil Towers’ 75th birthday.

  摘要：

  An enzyme from leaves of staghorn sumac (Rhus typhina) that catalysed the galloylation of 1,2,3,4, 6-penta-O-galloyl-beta-D-glucose to the gallotannin, 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-beta-D-glucose, was purified more than 500-fold to apparent homogeneity. beta-Glucogallin (1-O-galloyl-beta-D-glucopyranose) served as activated acyl donor in this conversion. For the native enzyme, a M(r) value of 170,000 was determined by gel filtration, while a single polypeptide band of M(r) 42,000 was detected by SDS-PAGE. The acyltransferase had pH and temperature optima of 4-4.5 and 25 degrees, respectively, and was most stable between pH 3 and 4.5. Besides the major substrate, pentagalloylglucose, also 1,2,3,6-tetragalloylglucose and hexa- to nona-substituted gallotannins were accepted as minor substrates by this new enzyme for which the systematic name "beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose (3-O-galloyl)-galloyltransferase" (EC 2.3.1.-) is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00014-4

文献信息

• Gallotannin biosynthesis: purification of β -glucogallin: 1,2,3,4,6-pentagalloyl- β -d-glucose galloyltransferase from sumac leaves fn1 fn1In honour of Professor G. H. Neil Towers’ 75th birthday.
  作者：Ruth Niemetz、Georg G Gross

  DOI：10.1016/s0031-9422(98)00014-4

  日期：1998.9

  An enzyme from leaves of staghorn sumac (Rhus typhina) that catalysed the galloylation of 1,2,3,4, 6-penta-O-galloyl-beta-D-glucose to the gallotannin, 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-beta-D-glucose, was purified more than 500-fold to apparent homogeneity. beta-Glucogallin (1-O-galloyl-beta-D-glucopyranose) served as activated acyl donor in this conversion. For the native enzyme, a M(r) value of 170,000 was determined by gel filtration, while a single polypeptide band of M(r) 42,000 was detected by SDS-PAGE. The acyltransferase had pH and temperature optima of 4-4.5 and 25 degrees, respectively, and was most stable between pH 3 and 4.5. Besides the major substrate, pentagalloylglucose, also 1,2,3,6-tetragalloylglucose and hexa- to nona-substituted gallotannins were accepted as minor substrates by this new enzyme for which the systematic name "beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose (3-O-galloyl)-galloyltransferase" (EC 2.3.1.-) is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.