p-nitrophenyl 2-O-methyl-α-D-galactopyranoside | 280136-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-O-methyl-α-D-galactopyranoside
• 英文别名: alpha-D-Galactopyranoside, 4-nitrophenyl 2-O-methyl-；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-5-methoxy-6-(4-nitrophenoxy)oxane-3,4-diol
• CAS: 280136-22-3
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: JCPHBVJZPWWKHF-SJHCENCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 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 4,6-O-benzylidene-α-D-galactopyranoside 在 sodium hydroxide 、 硫酸 、 sodium methylate 、 四丁基硫酸氢铵 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸酐 、 溶剂黄146 为溶剂， 20.0~125.0 ℃ 、506.62 kPa 条件下， 反应 113.08h， 生成 p-nitrophenyl 2-O-methyl-α-D-galactopyranoside
  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

• KOHLENHYDRATMODIFIZIERTE CYTOSTATIKA
  申请人：BAYER AG

  公开号：EP0819135B1

  公开（公告）日：1999-11-17
• US6271342B1
  申请人：——

  公开号：US6271342B1

  公开（公告）日：2001-08-07
• 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.