3-hydroxy-2,4-pentadione-5-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2,4-pentadione-5-phosphate
• 英文别名: 3-Hydroxy-2,4-dioxopentyl phosphate；(3-hydroxy-2,4-dioxopentyl) dihydrogen phosphate
• 化学式: C₅H₉O₇P
• 分子量: 212.096
• InChiKey: AKHNGSPNHAFBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2S)-1,4-二氧杂螺[4.5]癸-2-基-1,2-丙二酮 在 luxS regulated G 、 luxS regulated kinase 、 5’-三磷酸腺苷 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 以 water-d2 、 水 为溶剂， 反应 0.17h， 生成 3-hydroxy-2,4-pentadione-5-phosphate 、 3,4,4-trihydroxy-2-pentanone-5-phosphate
  参考文献：
  名称：

  Processing the Interspecies Quorum-sensing Signal Autoinducer-2 (AI-2)

  摘要：

  The molecule (S)-4,5-dihydroxy-2,3-pentanedione (DPD) is produced by many different species of bacteria and is the precursor of the signal molecule autoinducer-2 (AI-2). AI-2 mediates interspecies communication and facilitates regulation of bacterial behaviors such as biofilm formation and virulence. A variety of bacterial species have the ability to sequester and process the AI-2 present in their environment, thereby interfering with the cell-cell communication of other bacteria. This process involves the AI-2-regulated lsr operon, comprised of the Lsr transport system that facilitates uptake of the signal, a kinase that phosphorylates the signal to phospho-DPD (P-DPD), and enzymes (like LsrG) that are responsible for processing the phosphorylated signal. Because P-DPD is the intracellular inducer of the lsr operon, enzymes involved in P-DPD processing impact the levels of Lsr expression. Here we show that LsrG catalyzes isomerization of P-DPD into 3,4,4-trihydroxy-2-pentanone-5-phosphate. We present the crystal structure of LsrG, identify potential catalytic residues, and determine which of these residues affects P-DPD processing in vivo and in vitro. We also show that an lsrG deletion mutant accumulates at least 10 times more P-DPD than wild type cells. Consistent with this result, we find that the lsrG mutant has increased expression of the lsr operon and an altered profile of AI-2 accumulation and removal. Understanding of the biochemical mechanisms employed by bacteria to quench signaling of other species can be of great utility in the development of therapies to control bacterial behavior.

  DOI：

  10.1074/jbc.m111.230227

文献信息

• Processing the Interspecies Quorum-sensing Signal Autoinducer-2 (AI-2)
  作者：João C. Marques、Pedro Lamosa、Caitlin Russell、Rita Ventura、Christopher Maycock、Martin F. Semmelhack、Stephen T. Miller、Karina B. Xavier

  DOI：10.1074/jbc.m111.230227

  日期：2011.5

  The molecule (S)-4,5-dihydroxy-2,3-pentanedione (DPD) is produced by many different species of bacteria and is the precursor of the signal molecule autoinducer-2 (AI-2). AI-2 mediates interspecies communication and facilitates regulation of bacterial behaviors such as biofilm formation and virulence. A variety of bacterial species have the ability to sequester and process the AI-2 present in their environment, thereby interfering with the cell-cell communication of other bacteria. This process involves the AI-2-regulated lsr operon, comprised of the Lsr transport system that facilitates uptake of the signal, a kinase that phosphorylates the signal to phospho-DPD (P-DPD), and enzymes (like LsrG) that are responsible for processing the phosphorylated signal. Because P-DPD is the intracellular inducer of the lsr operon, enzymes involved in P-DPD processing impact the levels of Lsr expression. Here we show that LsrG catalyzes isomerization of P-DPD into 3,4,4-trihydroxy-2-pentanone-5-phosphate. We present the crystal structure of LsrG, identify potential catalytic residues, and determine which of these residues affects P-DPD processing in vivo and in vitro. We also show that an lsrG deletion mutant accumulates at least 10 times more P-DPD than wild type cells. Consistent with this result, we find that the lsrG mutant has increased expression of the lsr operon and an altered profile of AI-2 accumulation and removal. Understanding of the biochemical mechanisms employed by bacteria to quench signaling of other species can be of great utility in the development of therapies to control bacterial behavior.