autoinducer-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: autoinducer-2
• 英文别名: AI-2；(1R,5S,8S)-3,3-dihydroxy-5-methyl-2,4,6-trioxa-3-boranuidabicyclo[3.3.0]octane-1,8-diol
• 化学式: C₅H₁₀BO₇
• 分子量: 192.941
• InChiKey: ACKRRKSNOOISSG-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.75
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-二溴-5-羟基呋喃-2(5h)-酮 、 、 cycl.-cis-β-(p-Methoxy-benzoyl)-β-brom-acrylsaeure-methylester = β-Brom-γ-methoxy-γ-(p-methoxy-phenyl)-crotonlacton 、 、 4-{[3-Bromo-2-(4-methoxyphenyl)-5-oxo-2 5-dihydro-2-furanyl]oxy}benzoate 、 、 autoinducer-2 、 、 2,5-二甲基-4-羟基-3(2H)-呋喃酮 、 、 2,4-二苯基-2-甲氧基-3(2H)-呋喃酮[用于高效液相色谱标记] 、 、 2-戊基-2-环戊烯-1-酮 生成 4-bromo-5-(4-methoxyphenyl)-2(5H)-furanone
  参考文献：
  名称：

  Method of using autoinducer-2 as a periodontal disease marker

  摘要：

  包含自体诱导素2的用于确定牙周疾病发病时间的标记物和用于确定牙周疾病进展阶段的标记物。

  公开号：

  US08293478B2
• 作为产物：
  描述：

  6-甲基-2-硫代-2,3-二氢-4H-1,3-苯并噁嗪-4-酮 在 tetrahydroxo borate 作用下， 生成 autoinducer-2
  参考文献：
  名称：

  Serendipitous discovery of two highly selective inhibitors of bacterial luciferase

  摘要：

  Herein, we report the serendipitous discovery of two highly selective inhibitors of bacterial luciferase, N-phenacylthiazolium bromide (PTB) and pifithrin-alpha (PFT-alpha). These compounds, which are both derivatives of N-phenacylthiazolium salts, comprise a previously unreported class of luciferase inhibitors that are effective both in vitro and in live bacteria. Interestingly, although they are structurally similar, these compounds appear to elicit inhibitory effects via two different modes of action. Support for these conclusions has been obtained using purified luciferase enzyme as well as genetic knockout strains of Vibrio harveyi. Overall, this report provides the first evidence that N-phenacylthiazolium derivatives can serve as luciferase inhibitors, and also illustrates how the systematic investigation of logical hypotheses can lead to unexpected and potentially useful outcomes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.086

文献信息

• Ozonolysis of Alkynes—A Flexible Route to Alpha-Diketones: Synthesis of AI-2
  作者：Joshua L. Alterman、Dua X. Vang、Marissa Roghair Stroud、Larry J. Halverson、George A. Kraus

  DOI：10.1021/acs.orglett.0c02182

  日期：2020.10.2

  A mild procedure for the low-temperature conversion of alkynes to diketones has been developed and employed in the synthesis of AI-2.

  已经开发了一种温和的程序，用于将炔烃低温转化为二酮，并用于合成AI-2。
• Periodontal Disease Marker
  申请人：Souno Hatsumi

  公开号：US20120276546A1

  公开（公告）日：2012-11-01

  A marker for determining the onset of periodontal disease and a marker far determining the progression stage of periodontal disease, each containing autoinducer-2.

  一种用于确定牙周病发作的标记物和一种用于确定牙周病进展阶段的标记物，均含有自体诱导素-2。
• Periodontal Disease Marker (as amended herewith)
  申请人：Souno Hatsumi

  公开号：US20120015397A1

  公开（公告）日：2012-01-19

  A marker for determining the onset of periodontal disease and a marker for determining the progression stage of periodontal disease, each containing autoinducer-2.

  一种用于确定牙周疾病发病时机的标记物和一种用于确定牙周疾病进展阶段的标记物，均含有自体感应素-2。
• Method of selecting an agent that improves periodontal disease
  申请人：Souno Hatsumi

  公开号：US08568986B2

  公开（公告）日：2013-10-29

  A marker for determining the onset of periodontal disease and a marker far determining the progression stage of periodontal disease, each containing autoinducer-2.

  一种用于确定牙周病发病时机的标记物和一种用于确定牙周病进展阶段的标记物，均含有自体诱导素-2。
• Serendipitous discovery of two highly selective inhibitors of bacterial luciferase
  作者：Taehan Kim、David A. Spiegel

  DOI：10.1016/j.tet.2013.05.086

  日期：2013.9

  Herein, we report the serendipitous discovery of two highly selective inhibitors of bacterial luciferase, N-phenacylthiazolium bromide (PTB) and pifithrin-alpha (PFT-alpha). These compounds, which are both derivatives of N-phenacylthiazolium salts, comprise a previously unreported class of luciferase inhibitors that are effective both in vitro and in live bacteria. Interestingly, although they are structurally similar, these compounds appear to elicit inhibitory effects via two different modes of action. Support for these conclusions has been obtained using purified luciferase enzyme as well as genetic knockout strains of Vibrio harveyi. Overall, this report provides the first evidence that N-phenacylthiazolium derivatives can serve as luciferase inhibitors, and also illustrates how the systematic investigation of logical hypotheses can lead to unexpected and potentially useful outcomes. (C) 2013 Elsevier Ltd. All rights reserved.