1-cyclopropyl-3,4-dihydroxybutane-1,2-dione | 1203707-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopropyl-3,4-dihydroxybutane-1,2-dione
• 英文别名: 1-Cyclopropyl-3,4-dihydroxybutane-1,2-dione
• CAS: 1203707-85-0
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: QNSHQBHVJSPUDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-3,4-dihydroxybutane-1,2-dione 、 邻苯二胺 反应 0.17h， 生成 1-(3-cyclopropylquinoxalin-2-yl)ethane-1,2-diol
  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
• 作为产物：
  描述：

  Cyclopropyl-diazomethyl-keton 在 四丁基氟化铵 、 二甲基二环氧乙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-cyclopropyl-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

文献信息

• Synthetic Analogs Tailor Native AI-2 Signaling Across Bacterial Species
  作者：Varnika Roy、Jacqueline A. I. Smith、Jingxin Wang、Jessica E. Stewart、William E. Bentley、Herman O. Sintim

  DOI：10.1021/ja102587w

  日期：2010.8.18

  The widespread use of antibiotics and the emergence of resistant strains call for new approaches to treat bacterial infection. Bacterial cell cell communication or "quorum sensing" (QS) is mediated by "signatures" of small molecules that represent targets for "quenching" communication and avoiding virulent phenotypes. Only a handful of small molecules that antagonize the action of the "universal" autoinducer, Al-2, have been reported. The biological basis of antagonism, as well as the targets for these select few Al-2 antagonists, have not been clearly defined. We have developed C-1 alkyl analogs of Al-2 that quench the OS response in multiple bacterial species simultaneously. We also demonstrate the biological basis for this action. Like Al-2, the analogs are activated by the bacterial kinase, LsrK, and modulate Al-2 specific gene transcription through the transcriptional regulator, LsrR. Interestingly, addition of a single carbon to the C1-alkyl chain of the analog plays a crucial role in determining the effect of the analog on the QS response. While an ethyl modified analog is an agonist, propyl becomes an antagonist of the QS circuit. In a trispecies synthetic ecosystem comprised of E. coli, S. typhimurium, and V. harveyi we discovered both cross-species and species-specific anti-Al-2 QS activities. Our results suggest entirely new modalities for interrupting or tailoring the network of communication among bacteria.
• US8952192B2
  申请人：——

  公开号：US8952192B2

  公开（公告）日：2015-02-10
• 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
  作者：Jacqueline A. I. Smith、Jingxin Wang、Sao-Mai Nguyen-Mau、Vincent Lee、Herman O. Sintim

  DOI：10.1039/b909666c

  日期：——

  C1-alkyl AI-2 analogues do not induce bioluminescence in V. harveyi on their own but enhance the bioluminescence induced by AI-2 in a synergistic fashion. A new facile synthesis of AI-2 facilitates the synthesis of a diverse set of AI-2 analogues and biological screening suggests that receptors that are involved in the synergistic bioluminescence production in V. harveyi are promiscuous.

  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。
• Altering the Communication Networks of Multispecies Microbial Systems Using a Diverse Toolbox of AI-2 Analogues
  作者：Sonja Gamby、Varnika Roy、Min Guo、Jacqueline A. I. Smith、Jingxin Wang、Jessica E. Stewart、Xiao Wang、William E. Bentley、Herman O. Sintim

  DOI：10.1021/cb200524y

  日期：2012.6.15

  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.