6-O-(4-O-n-dodecylbut-2-yn-1-yl)-α-D-galactopyranose | 1108749-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(4-O-n-dodecylbut-2-yn-1-yl)-α-D-galactopyranose
• 英文别名: (2S,3R,4S,5R,6R)-6-(4-dodecoxybut-2-ynoxymethyl)oxane-2,3,4,5-tetrol
• CAS: 1108749-19-4
• 化学式: C₂₂H₄₀O₇
• 分子量: 416.555
• InChiKey: PULCWWJRUSBGHA-CTWRKMMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  alpha-D-半乳糖 在 硫酸 、 水 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醚 、 二甲基亚砜 、 甲苯 为溶剂， 反应 17.0h， 生成 6-O-(4-O-n-dodecylbut-2-yn-1-yl)-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis, surface tension properties and antibacterial activities of amphiphilic d -galactopyranose derivatives

  摘要：

  Several amphiphilic D-galactopyranose derivatives were synthesized in which the glycosidic moiety was separated from the hydrophobic alkyl chain (along 8 or 12 carbon atoms) by a spacer arm (butyl, butynyl or benzyl) in order to increase their surfactant properties and to obtain new antibacterial compounds. The surface tensions of the products were analyzed by Critical Micelle Concentration (CMC) and gamma(CMC) measurements and the antimicrobial activities were assayed against 10 bacterial species by Minimum Inhibitory Concentration (MIC) determination in liquid broth. The introduction of an aliphatic spacer arm increased the amphiphilic properties of the compounds and the CMC values were 40-500 times lower than their analogs without spacer arm. In the same manner, the spacer arms significantly increased the antibacterial power of the compounds. The products 4d and 4e exhibiting a C12 alkyl chain and an aliphatic spacer arm (butyl and butynyl) were the best surfactants (CMC = 0.023 and 0.032 mmol/L, respectively) and presented also the best antibacterial activities (MIC = 15.62 and 3.91 mu g/mL for Micrococcus luteus, respectively). But the antibacterial activity of the newly synthesized products seemed to depend more on the cell wall composition of the bacteria than only on the amphiphilic character of the compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.032

文献信息

• Synthesis, surface tension properties and antibacterial activities of amphiphilic d -galactopyranose derivatives
  作者：Ludovic Chaveriat、Isabelle Gosselin、Cécile Machut、Patrick Martin

  DOI：10.1016/j.ejmech.2012.12.032

  日期：2013.4

  Several amphiphilic D-galactopyranose derivatives were synthesized in which the glycosidic moiety was separated from the hydrophobic alkyl chain (along 8 or 12 carbon atoms) by a spacer arm (butyl, butynyl or benzyl) in order to increase their surfactant properties and to obtain new antibacterial compounds. The surface tensions of the products were analyzed by Critical Micelle Concentration (CMC) and gamma(CMC) measurements and the antimicrobial activities were assayed against 10 bacterial species by Minimum Inhibitory Concentration (MIC) determination in liquid broth. The introduction of an aliphatic spacer arm increased the amphiphilic properties of the compounds and the CMC values were 40-500 times lower than their analogs without spacer arm. In the same manner, the spacer arms significantly increased the antibacterial power of the compounds. The products 4d and 4e exhibiting a C12 alkyl chain and an aliphatic spacer arm (butyl and butynyl) were the best surfactants (CMC = 0.023 and 0.032 mmol/L, respectively) and presented also the best antibacterial activities (MIC = 15.62 and 3.91 mu g/mL for Micrococcus luteus, respectively). But the antibacterial activity of the newly synthesized products seemed to depend more on the cell wall composition of the bacteria than only on the amphiphilic character of the compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.