2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone | 325484-28-4

• 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: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone
• 英文别名: 4-methylumbelliferyl (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1→3)-2,4,6-tri-O-acetyl-α-D-mannopyranoside
• CAS: 325484-28-4
• 化学式: C₃₆H₄₂O₂₀
• 分子量: 794.717
• InChiKey: WQGABBLJGZUDHN-SFACUBCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  251.23
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone
  参考文献：
  名称：

  拟杆菌属细菌GH99糖苷水解酶的内切α-1,2-甘露聚糖酶活性的结构和动力学分析。

  摘要：

  糖苷水解酶家族99（GH99）的创建是为了对具有内切α-甘露糖苷酶活性的序列相关糖苷酶进行分类：真核N-聚糖前体（Glc 1-3 Man 9 GlcNAc 2）中甘露糖苷键的裂解，释放单，双-和triglucosylated甘露糖（GLC 1-3 -1,3-曼）。GH99家族成员最近与拟杆菌的能力有关 spp.spp。，存在于肠道菌群内，通过分解分支内的αMan-1,3-αMan→1,2-αMan-1,2-αMan序列来代谢真菌细胞壁α-甘露聚糖，从而释放α-1,3-甘露二糖偏离主要的α-1,6-甘露聚糖骨架。我们报告了一系列底物和抑制剂的开发，我们将其用于在动力学和结构上表征细菌拟南芥（Theactotaides thetaiotaomicron）和xylanisolvens的细菌GH99酶的这种新型内-α-1,2-甘露聚糖酶活性。这些数据表明大约为5 kJ mol -1对-2子位点中相

  DOI：

  10.1002/chem.201405539
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl-(1-3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose 在 palladium on activated charcoal 吡啶 、 氢气 、 zinc(II) chloride 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 144.0h， 生成 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone
  参考文献：
  名称：

  Synthesis of α-D-Glucopyranosyl-(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for Endo-α-1,2-Mannosidase

  摘要：

  alpha -D-Glucopyranosyl-(1-3)-alpha -D-mannopyranosyl-(1-7)-4-methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-alpha -1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta -glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-beta -mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated alpha -D-glucopyranosyl-(1-3)-alpha -D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as st substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the alpha -glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 mug and with time up to 2 h. V-max and K-m were determined to be 0.17 nmol/mg x h and 3.7 mM, respectively.

  DOI：

  10.1080/07328300008544148