D-galactonoamidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: D-galactonoamidine
• 英文别名: (2R,3S,4S,5S)-6-amino-2-(hydroxymethyl)-2,3,4,5-tetrahydropyridine-3,4,5-triol
• 化学式: C₆H₁₂N₂O₄
• 分子量: 176.172
• InChiKey: KIFBXZRNIGNERW-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以100%的产率得到D-galactonoamidine
  参考文献：
  名称：

  Structure–Activity Relationship of Highly Potent Galactonoamidine Inhibitors toward β-Galactosidase (Aspergillus oryzae)

  摘要：

  A small library of 22 N-substituted galactonoamidines was synthesized, and their structure-activity relationship for inhibition of the hydrolytic activity of beta-galactosidase (Aspergillus oryzae) was evaluated. A fast screening assay in 96-well plate format was used to follow the enzymatic hydrolysis of 2-chloro-4-nitrophenyl-beta-d-galactopyranoside using UV-vis spectroscopy. The aglycon moiety of all compounds was found to have a profound effect on their inhibitory ability. In general, galactonoamidines derived from cyclic aliphatic and linear amines show higher inhibition activity than those derived from benzylamines. Hydrophobic interactions of the methyl group rather than pi-pi stacking interactions of the aromatic ring in p-methylbenzyl-d-galactonoamidine were identified to cause its transition-state-like character and the remarkably high inhibitory ability (K-i = 8 nM). A flexible 3-carbon methylene spacer between the exo N atom of the sugar moiety and a phenyl group furthermore increased the observed apparent inhibition drastically

  DOI：

  10.1021/jm501111y

文献信息

• Papandreou; Tong; Ganem, Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 11682 - 11690
  作者：Papandreou、Tong、Ganem

  DOI：——

  日期：——
• Structure–Activity Relationship of Highly Potent Galactonoamidine Inhibitors toward β-Galactosidase (<i>Aspergillus oryzae</i>)
  作者：Qiu-Hua Fan、Kailey A. Claunch、Susanne Striegler

  DOI：10.1021/jm501111y

  日期：2014.11.13

  A small library of 22 N-substituted galactonoamidines was synthesized, and their structure-activity relationship for inhibition of the hydrolytic activity of beta-galactosidase (Aspergillus oryzae) was evaluated. A fast screening assay in 96-well plate format was used to follow the enzymatic hydrolysis of 2-chloro-4-nitrophenyl-beta-d-galactopyranoside using UV-vis spectroscopy. The aglycon moiety of all compounds was found to have a profound effect on their inhibitory ability. In general, galactonoamidines derived from cyclic aliphatic and linear amines show higher inhibition activity than those derived from benzylamines. Hydrophobic interactions of the methyl group rather than pi-pi stacking interactions of the aromatic ring in p-methylbenzyl-d-galactonoamidine were identified to cause its transition-state-like character and the remarkably high inhibitory ability (K-i = 8 nM). A flexible 3-carbon methylene spacer between the exo N atom of the sugar moiety and a phenyl group furthermore increased the observed apparent inhibition drastically