藤黄菌素-3’,7-二-O-葡糖苷 | 52187-80-1

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 藤黄菌素-3’,7-二-O-葡糖苷
• 中文别名: 藤黄菌素-3',7-二-O-葡糖苷
• 英文名称: luteolin 3',7-diglucoside
• 英文别名: luteolin 3',7-di-O-glucoside；Luteolin-3',7-di-O-glucoside；5-hydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 52187-80-1
• 化学式: C₂₇H₃₀O₁₆
• 分子量: 610.526
• InChiKey: BISZYPSIZGKOFA-IPOZFMEPSA-N

物化性质

• 熔点：
  220-250°C
• 沸点：
  998.0±65.0 °C(Predicted)
• 密度：
  1.742±0.06 g/cm3(Predicted)
• LogP：
  -3.490 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline 、 藤黄菌素-3’,7-二-O-葡糖苷 在 endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以70%的产率得到
  参考文献：
  名称：

  Introducing N-glycans into natural products through a chemoenzymatic approach

  摘要：

  The present study describes an efficient chemoenzymatic method for introducing a core N-glycan of glycoprotein origin into various lipophilic natural products. It was found that the endo-beta-N-acetylglucosaminidase from Arthrobactor protophormiae (Endo-A) had broad substrate specificity and can accommodate a wide range of glucose (Glc)- or N-acetylglucosamine (GIcNAc)-containirig natural products as acceptors for transglycosylation, when an N-glycan oxazoline Was used as a donor substrate. Using lithocholic acid as a model compound, we have shown that introduction of an N-glycan could be achieved by a two-step approach: chemical glycosylation to introduce a monosaccharide (GIc or GIcNAc) as a handle, and then Endo-A catalyzed transglycosylation to accomplish the site-specific N-glycan attachment. For those natural products that already carry terminal GIc or GIcNAc residues, direct enzymatic transglycosylation using sugar oxazoline as the donor substrate was achievable to introduce an N-glycan. It was also demonstrated that simultaneous double glycosylation could be fulfilled when the natural product contains two GIc residues. This chemoenzymatic method is concise, site-specific, and highly convergent. Because N-glycans of glycoprotein origin can serve as ligands for diverse lectins and cell-surface receptors, introduction of a defined N-glycan into biologically significant natural products may bestow novel properties onto these natural products for drug discovery and development. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.033

文献信息

• Introducing N-glycans into natural products through a chemoenzymatic approach
  作者：Wei Huang、Hirofumi Ochiai、Xinyu Zhang、Lai-Xi Wang

  DOI：10.1016/j.carres.2008.08.033

  日期：2008.11

  The present study describes an efficient chemoenzymatic method for introducing a core N-glycan of glycoprotein origin into various lipophilic natural products. It was found that the endo-beta-N-acetylglucosaminidase from Arthrobactor protophormiae (Endo-A) had broad substrate specificity and can accommodate a wide range of glucose (Glc)- or N-acetylglucosamine (GIcNAc)-containirig natural products as acceptors for transglycosylation, when an N-glycan oxazoline Was used as a donor substrate. Using lithocholic acid as a model compound, we have shown that introduction of an N-glycan could be achieved by a two-step approach: chemical glycosylation to introduce a monosaccharide (GIc or GIcNAc) as a handle, and then Endo-A catalyzed transglycosylation to accomplish the site-specific N-glycan attachment. For those natural products that already carry terminal GIc or GIcNAc residues, direct enzymatic transglycosylation using sugar oxazoline as the donor substrate was achievable to introduce an N-glycan. It was also demonstrated that simultaneous double glycosylation could be fulfilled when the natural product contains two GIc residues. This chemoenzymatic method is concise, site-specific, and highly convergent. Because N-glycans of glycoprotein origin can serve as ligands for diverse lectins and cell-surface receptors, introduction of a defined N-glycan into biologically significant natural products may bestow novel properties onto these natural products for drug discovery and development. (C) 2008 Elsevier Ltd. All rights reserved.