1-cyclohexyl-2-diazo-3,4-dihydroxybutan-1-one | 1203708-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-2-diazo-3,4-dihydroxybutan-1-one
• CAS: 1203708-03-5
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: TYHXOGFIXVPTSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.93
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-2-diazo-3,4-dihydroxybutan-1-one 在 二甲基二环氧乙烷 作用下， 生成 1-cyclohexyl-3,4-dihydroxybutane-1,2-dione
  参考文献：
  名称：

  Altering the Communication Networks of Multispecies Microbial Systems Using a Diverse Toolbox of AI-2 Analogues

  摘要：

  There have been intensive efforts to find small molecule antagonists for bacterial quorum sensing (QS) mediated by the "universal" QS autoinducer, AI-2. Previous work has shown that linear and branched aryl analogues of AI-2 can selectively modulate AI-2 signaling in bacteria. Additionally, LsrK-dependent phosphorylated analogues have been implicated as the active inhibitory form against AI-2 signaling. We used these observations to synthesize an expanded and diverse array of AI-2 analogues, which included aromatic as well as cyclic C-1-alkyl analogues. Species-specific analogues that disrupted AI-2 signaling in Escherichia coli and Salmonella typhimurium were identified. Similarly, analogues that disrupted QS behaviors in Pseudomonas aeruginosa were found. Moreover, we observed a strong correlation between LsrK-dependent phosphorylation of these acyl analogues and their ability to suppress QS. Significantly, we demonstrate that these analogues can selectively antagonize QS in single bacterial strains in a physiologically relevant polymicrobial culture.

  DOI：

  10.1021/cb200524y
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-cyclohexyl-2-diazo-3,4-dihydroxybutan-1-one
  参考文献：
  名称：

  Biological screening of a diverse set of AI-2 analogues in Vibrio harveyi suggests that receptors which are involved in synergistic agonism of AI-2 and analogues are promiscuous

  摘要：

  C1-烷基AI-2类似物单独不会诱导V. harveyi的生物发光，但会以协同方式增强AI-2诱导的生物发光。AI-2的新简易合成方法便于合成多种AI-2类似物，生物筛选结果表明，参与V. harveyi协同生物发光产生的受体是多重性的。

  DOI：

  10.1039/b909666c