deoxy-Isobutyl DPD | 1242413-40-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: deoxy-Isobutyl DPD
• 英文别名: 2-Hydroxy-6-methylheptane-3,4-dione
• CAS: 1242413-40-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: SZFVMQWOAWXRRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  deoxy-Isobutyl DPD 、 邻苯二胺 反应 0.17h， 生成 1-(3-isobutylquinoxalin-2-yl)ethanol
  参考文献：
  名称：

  Synthetic Analogs Tailor Native AI-2 Signaling Across Bacterial Species

  摘要：

  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.

  DOI：

  10.1021/ja102587w
• 作为产物：
  描述：

  3-diazo-2-hydroxy-6-methylheptan-4-one 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 生成 deoxy-Isobutyl DPD
  参考文献：
  名称：

  Synthetic Analogs Tailor Native AI-2 Signaling Across Bacterial Species

  摘要：

  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.

  DOI：

  10.1021/ja102587w

文献信息

• Phosphorylated and Branched Dihydroxy-Pentane-Dione (DPD) Analogs as Quorum Sensing Inhibitors in Bacteria
  申请人：Sintim Herman

  公开号：US20120294900A1

  公开（公告）日：2012-11-22

  Provided are compositions and methods for modulating quorum sensing in microbes. The compounds are AI-2 analogs and as such have structures similar to 4,5-dihydroxy-2,3-pentanedione that can act as agonists/antagonists of quorum sensing. The compounds are useful for modulating quorum sensing in bacteria and can be used in methods for prophylaxis or therapy of bacterial infections and for reduction of biofilms.

  提供了一种调节微生物群体感应的组合物和方法。这些化合物是AI-2类似物，因此具有类似于4,5-二羟基-2,3-戊二酮的结构，可以作为微生物群体感应的激动剂/拮抗剂。这些化合物对调节细菌的群体感应很有用，并可用于预防或治疗细菌感染以及减少生物膜的方法中。
• US8952192B2
  申请人：——

  公开号：US8952192B2

  公开（公告）日：2015-02-10
• 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.