(2Z)-8-((2-carbamoylphenyl)amino)-3,7-dimethylocta-2,6-dien-1-yl acetate | 1450602-08-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z)-8-((2-carbamoylphenyl)amino)-3,7-dimethylocta-2,6-dien-1-yl acetate
• CAS: 1450602-08-0
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: YVHGBBFXMSLIPM-ZDVBIRFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2Z)-8-((2-carbamoylphenyl)amino)-3,7-dimethylocta-2,6-dien-1-yl acetate 在 三溴化磷 、 potassium carbonate 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 48.25h， 生成
  参考文献：
  名称：

  Fluorescent probes for investigation of isoprenoid configuration and size discrimination by bactoprenol-utilizing enzymes

  摘要：

  Undecaprenyl Pyrophosphate Synthase (UPPS) is an enzyme critical to the production of complex polysaccharides in bacteria, as it produces the crucial bactoprenol scaffold on which these materials are assembled. Methods to characterize the systems associated with polysaccharide production are non-trivial, in part due to the lack of chemical tools to investigate their assembly. In this report, we develop a new fluorescent tool using UPPS to incorporate a powerful fluorescent anthranilamide moiety into bactoprenol. The activity of this analogue in polysaccharide biosynthesis is then tested with the initiating hexose-1-phosphate transferases involved in Capsular Polysaccharide A biosynthesis in the symbiont Bacteroides fragilis and the asparagine-linked glycosylation system of the pathogenic Campylobacter jejuni. In addition, it is shown that the UPPS used to make this probe is not specific for E-configured isoprenoid substrates and that elongation by UPPS is required for activity with the downstream enzymes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.007
• 作为产物：
  描述：

  顺-3,7-二甲基-2,6-辛二烯-1-醇乙酸酯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 水杨酸 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 72.0h， 生成 (2Z)-8-((2-carbamoylphenyl)amino)-3,7-dimethylocta-2,6-dien-1-yl acetate
  参考文献：
  名称：

  Fluorescent probes for investigation of isoprenoid configuration and size discrimination by bactoprenol-utilizing enzymes

  摘要：

  Undecaprenyl Pyrophosphate Synthase (UPPS) is an enzyme critical to the production of complex polysaccharides in bacteria, as it produces the crucial bactoprenol scaffold on which these materials are assembled. Methods to characterize the systems associated with polysaccharide production are non-trivial, in part due to the lack of chemical tools to investigate their assembly. In this report, we develop a new fluorescent tool using UPPS to incorporate a powerful fluorescent anthranilamide moiety into bactoprenol. The activity of this analogue in polysaccharide biosynthesis is then tested with the initiating hexose-1-phosphate transferases involved in Capsular Polysaccharide A biosynthesis in the symbiont Bacteroides fragilis and the asparagine-linked glycosylation system of the pathogenic Campylobacter jejuni. In addition, it is shown that the UPPS used to make this probe is not specific for E-configured isoprenoid substrates and that elongation by UPPS is required for activity with the downstream enzymes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.007