p-nitrophenyl 4-O-methyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 4-O-methyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4R,5S,6R)-6-(hydroxymethyl)-5-methoxy-2-(4-nitrophenoxy)oxane-3,4-diol
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: UYWBOXJHLVLDIG-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 硫酸 、 水 、 氢气 、 溶剂黄146 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 乙酸酐 、 溶剂黄146 为溶剂， 20.0~125.0 ℃ 、506.62 kPa 条件下， 反应 21.08h， 生成 p-nitrophenyl 4-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.