Pr-DPD | 1173172-83-2

• 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: Pr-DPD
• 英文别名: (S)-1,2-dihydroxyheptane-3,4-dione；propyl-DPD；(2S)-1,2-dihydroxyheptane-3,4-dione
• CAS: 1173172-83-2
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: LHCGIMVMEOPNPW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• 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

• 作为产物：
  描述：

  (S)-1,2-cyclohexylidenedioxy-3,4-heptadione 在 氘代硫酸 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 反应 6.0h， 以64%的产率得到Pr-DPD
  参考文献：
  名称：

  An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues

  摘要：

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.

  DOI：

  10.1021/ja802353j

文献信息

• An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues
  作者：Colin A. Lowery、Junguk Park、Gunnar F. Kaufmann、Kim D. Janda

  DOI：10.1021/ja802353j

  日期：2008.7.1

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.
• Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs
  作者：Hadas Ganin、Xu Tang、Michael M. Meijler

  DOI：10.1016/j.bmcl.2009.03.163

  日期：2009.7

  Autoinducer-2 (AI-2) has been suggested to serve as a universal interspecies quorum sensing signaling molecule. We have synthesized a set of AI-2 analogs with small incremental changes in alkyl substitution on C-2 and evaluated them for their agonistic and antagonistic potential as quorum sensing (QS) attenuators in two different bacterial species: Pseudomonas aeruginosa and Vibrio harveyi. Unexpectedly, several of the analogs were found to function as synergistic QS agonists in V. harveyi, while two of these analogs inhibit QS in P. aeruginosa. (C) 2009 Elsevier Ltd. All rights reserved.