N,N-di(2-hydroxyethyl)-β-D-glucopyranosylamine | 95094-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-di(2-hydroxyethyl)-β-D-glucopyranosylamine
• 英文别名: N,N-di(2-hydroxyethyl)-β-D-glucosylamine；DHEtGPA；N,N-bis-(2-hydroxy-ethyl)-β-D-glucopyranosylamine；N,N-Bis-(2-hydroxy-aethyl)-β-D-glucopyranosylamin；(2R,3R,4S,5S,6R)-2-[bis(2-hydroxyethyl)amino]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 95094-03-4
• 化学式: C₁₀H₂₁NO₇
• 分子量: 267.279
• InChiKey: QESYUNJKZCCKRH-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  134
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-di(2-hydroxyethyl)-β-D-glucopyranosylamine 在 乙醇 、 丙二酸二乙酯 作用下， 生成 1-[bis-(2-hydroxy-ethyl)-amino]-1-deoxy-D-fructose
  参考文献：
  名称：

  The Amadori Rearrangement under New Conditions and its Significance for Non-enzymatic Browning Reactions²

  摘要：

  DOI：

  10.1021/ja01098a019
• 作为产物：
  描述：

  D-葡萄糖 、 二乙醇胺 以 甲醇 为溶剂， 反应 7.0h， 以91.3%的产率得到N,N-di(2-hydroxyethyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

  摘要：

  Various glucosylamines were synthesized from glucose and different alkyl amine compounds. These amino compounds are P-D-glucopyranosylamine (GPA), N-ethyl-beta-D-glucopyranosylamine (EtGPA), N-butyl-beta-D-glucopyranosylamine (BuGPA), N-hexyl-beta-D-glucopyranosylamine (HeGPA), N-octyl-beta-D-glucopyranosylamine (OcGPA), N-dodecyl-beta-D-glucopyranosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucopyranosylamine (HEtGPA) and N,N-di(2-hydroxyethyl)-beta-D-glucopyranosylamine (DHEtGPA). They were tested for their antifungal activity against the growth of Coriolus versicolor and Poria placenta. An improvement of the antifungal activity with the increase of alkyl chain length was observed. DoGPA exhibited the best antifungal activity against both strains. It completely inhibited the fungal growth at 0.01 x 10(-3) mol mL(-1) and 0.0075 x 10-3 Mol mL(-1) for C. versicolor and P. placenta, respectively. For other glucosylamines higher concentrations were needed for complete inhibition of fungi. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.005

文献信息

• N-Glycosyl Derivatives of Secondary Amines
  作者：John E. Hodge、Carl E. Rist

  DOI：10.1021/ja01126a042

  日期：1952.3
• Synthesis of<i>N</i>-Alkyl-β-<scp>d</scp>-glucosylamines and Their Antimicrobial Activity against<i>Fusarium proliferatum</i>,<i>Salmonella</i><i>typhimurium</i>, and<i>Listeria innocua</i>
  作者：T. Muhizi、S. Grelier、V. Coma

  DOI：10.1021/jf9016114

  日期：2009.12.9

  In this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.
• The Amadori Rearrangement under New Conditions and its Significance for Non-enzymatic Browning Reactions²
  作者：John E. Hodge、Carl E. Rist

  DOI：10.1021/ja01098a019

  日期：1953.1
• Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta
  作者：Théoneste Muhizi、Véronique Coma、Stéphane Grelier

  DOI：10.1016/j.carres.2008.07.005

  日期：2008.9

  Various glucosylamines were synthesized from glucose and different alkyl amine compounds. These amino compounds are P-D-glucopyranosylamine (GPA), N-ethyl-beta-D-glucopyranosylamine (EtGPA), N-butyl-beta-D-glucopyranosylamine (BuGPA), N-hexyl-beta-D-glucopyranosylamine (HeGPA), N-octyl-beta-D-glucopyranosylamine (OcGPA), N-dodecyl-beta-D-glucopyranosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucopyranosylamine (HEtGPA) and N,N-di(2-hydroxyethyl)-beta-D-glucopyranosylamine (DHEtGPA). They were tested for their antifungal activity against the growth of Coriolus versicolor and Poria placenta. An improvement of the antifungal activity with the increase of alkyl chain length was observed. DoGPA exhibited the best antifungal activity against both strains. It completely inhibited the fungal growth at 0.01 x 10(-3) mol mL(-1) and 0.0075 x 10-3 Mol mL(-1) for C. versicolor and P. placenta, respectively. For other glucosylamines higher concentrations were needed for complete inhibition of fungi. (C) 2008 Elsevier Ltd. All rights reserved.