(2R,4S)-2-甲基二氢-2,3,3,4(2H)-呋喃四醇 | 791810-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,4S)-2-甲基二氢-2,3,3,4(2H)-呋喃四醇
• 英文名称: (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran
• 英文别名: (2R,4S)-2-methyloxolane-2,3,3,4-tetrol
• CAS: 791810-94-1
• 化学式: C₅H₁₀O₅
• 分子量: 150.13
• InChiKey: BVIYGXUQVXBHQS-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one 、 水 生成 (2R,4S)-2-甲基二氢-2,3,3,4(2H)-呋喃四醇
  参考文献：
  名称：

  Salmonella typhimurium Recognizes a Chemically Distinct Form of the Bacterial Quorum-Sensing Signal AI-2

  摘要：

  Bacterial populations use cell-cell communication to coordinate community-wide regulation of processes such as biofilm formation, virulence, and bioluminescence. This phenomenon, termed quorum sensing, is mediated by small molecule signals known as autoinducers. While most autoinducers are species specific autoinducer-2 (AI-2), first identified in the marine bacterium Vibrio harveyi, is produced and detected by many Gram-negative and Gram-positive bacteria. The crystal structure of the V. harveyi AI-2 signaling molecule bound to its receptor protein revealed an unusual furanosyl borate diester. Here, we present the crystal structure of a second AI-2 signal binding protein, LsrB from Salmonella typhimurium. We find that LsrB binds a chemically distinct form of the AI-2 signal, (2R,4S)2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran (R-THMF), that lacks boron. Our results demonstrate that two different species of bacteria recognize two different forms of the autoinducer signal, both derived from 4,5-dihydroxy-2,3-pentanedione (DPD), and reveal new sophistication in the chemical lexicon used by bacteria in interspecies signaling.

  DOI：

  10.1016/j.molcel.2004.07.020

文献信息

• Salmonella typhimurium Recognizes a Chemically Distinct Form of the Bacterial Quorum-Sensing Signal AI-2
  作者：Stephen T. Miller、Karina B. Xavier、Shawn R. Campagna、Michiko E. Taga、Martin F. Semmelhack、Bonnie L. Bassler、Frederick M. Hughson

  DOI：10.1016/j.molcel.2004.07.020

  日期：2004.9

  Bacterial populations use cell-cell communication to coordinate community-wide regulation of processes such as biofilm formation, virulence, and bioluminescence. This phenomenon, termed quorum sensing, is mediated by small molecule signals known as autoinducers. While most autoinducers are species specific autoinducer-2 (AI-2), first identified in the marine bacterium Vibrio harveyi, is produced and detected by many Gram-negative and Gram-positive bacteria. The crystal structure of the V. harveyi AI-2 signaling molecule bound to its receptor protein revealed an unusual furanosyl borate diester. Here, we present the crystal structure of a second AI-2 signal binding protein, LsrB from Salmonella typhimurium. We find that LsrB binds a chemically distinct form of the AI-2 signal, (2R,4S)2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran (R-THMF), that lacks boron. Our results demonstrate that two different species of bacteria recognize two different forms of the autoinducer signal, both derived from 4,5-dihydroxy-2,3-pentanedione (DPD), and reveal new sophistication in the chemical lexicon used by bacteria in interspecies signaling.