6-甲基-2-硫代-2,3-二氢-4H-1,3-苯并噁嗪-4-酮 | 710324-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-甲基-2-硫代-2,3-二氢-4H-1,3-苯并噁嗪-4-酮
• 中文别名: (4S)-4,5-二羟基-2,3-戊二酮
• 英文名称: 4,5-dihydroxy-2,3-pentanedione
• 英文别名: (4S)-4,5-dihydroxy-2,3-pentanedione；(4S)-DPD；DPD；(S)-4,5-dihydroxypentane-2,3-dione；(4S)-4,5-dihydroxypentane-2,3-dione
• CAS: 710324-30-4
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: UYTRITJAZOPLCZ-BYPYZUCNSA-N

物化性质

• 沸点：
  263.0±30.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 在 sodium periodate 、 (-)-(S)-alpine-borane 、 ruthenium(IV) oxide hydrate 、 硫酸 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 生成 6-甲基-2-硫代-2,3-二氢-4H-1,3-苯并噁嗪-4-酮
  参考文献：
  名称：

  An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

  摘要：

  Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.036

文献信息

• Catalytic Mechanism of <i>S</i>-Ribosylhomocysteinase (LuxS):  Direct Observation of Ketone Intermediates by ¹³C NMR Spectroscopy
  作者：Jinge Zhu、Xubo Hu、Eric Dizin、Dehua Pei

  DOI：10.1021/ja0369663

  日期：2003.11.1

  and kinetic competence was demonstrated. The results support a catalytic mechanism in which the metal ion catalyzes an internal redox reaction, shifting the carbonyl group from the C-1 position to the C-3 position. Subsequent beta-elimination at the C-4 and C-5 positions releases homocysteine as a free thiol. The results also suggest that Cys-84 and Glu-57 are the possible general acids/bases for proton

  S-核糖同型半胱氨酸酶 (LuxS) 催化 S-核糖同型半胱氨酸 (SRH) 的硫醚键断裂，产生 l-同型半胱氨酸和 4,5-二羟基-2,3-戊二酮 (DHPD)。这是革兰氏阳性菌和革兰氏阴性菌中 II 型自诱导剂 (AI-2) 生物合成途径的关键步骤。先前的研究表明，LuxS 含有催化必需的 Fe2+ 离子。使用 2-和 3-13C-标记的 SRH 作为底物和 13C NMR 光谱研究了 LuxS 的催化机制。这些研究揭示了催化途径中存在 2- 和 3- 酮中间体。化学合成了 2-酮中间体，并证明了其化学和动力学能力。结果支持金属离子催化内部氧化还原反应的催化机制，将羰基从 C-1 位置移动到 C-3 位置。随后在 C-4 和 C-5 位置进行 β-消除将高半胱氨酸作为游离硫醇释放。结果还表明，Cys-84 和 Glu-57 是催化过程中质子转移的可能的通用酸/碱，并且酮中间体在重新结合和反应完成之前从酶活性位点释放。
• [EN] EXPEDITIOUS SYNTHESIS OF DPD<br/>[FR] SYNTHESE RAPIDE DE DPD
  申请人：UNIV PRINCETON

  公开号：WO2006034269A1

  公开（公告）日：2006-03-30

  This invention provides a practical synthesis route for 4,5-dihydroxypentane-2,3-dione (DPD), an unstable small molecule which is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis route includes new intermediates and allows preparation of isotopically-labeled DPD and ent-DPD. The method provides sufficient quantities of DPD for study of spontaneous binding of borate to DPD, the signal for the marine bacteria V. harveyi

  这项发明提供了一种实用的合成途径，用于合成4,5-二羟基戊烷-2,3-二酮（DPD），这是一种不稳定的小分子，被认为是细菌群体感应通用信号物质的来源。该合成途径包括新的中间体，并允许制备同位素标记的DPD和ent-DPD。该方法提供了足够数量的DPD，以研究硼酸与DPD的自发结合，这是海洋细菌V. harveyi的信号。
• Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2
  作者：Marine Frezza、Laurent Soulère、Damien Balestrino、Michel Gohar、Christian Deshayes、Yves Queneau、Christiane Forestier、Alain Doutheau

  DOI：10.1016/j.bmcl.2006.11.076

  日期：2007.3

  Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD), was prepared both as a racemic mixture and in the optically active form found in naturally occurring DPD. It was shown to exhibit the same ability as DPD to induce bioluminescence in Vibrio harveyi and beta-galactosidase activity in Salmonella enterica Typhimurium, both gram-negative bacteria. Likewise, it was also

  Ac2-DPD是4,5-二羟基-2,3-戊二酮（DPD）的双-（O）-乙酰化衍生物，既可以作为外消旋混合物，也可以天然存在于DPD中的旋光形式制备。它显示出与DPD相同的诱导哈维氏弧菌生物发光和肠炎沙门氏菌（Salmonella enterica Typhimurium）革兰氏阴性细菌中β-半乳糖苷酶活性的能力。同样，它也显示出抑制革兰氏阳性蜡样芽胞杆菌中生物膜的形成。最可能的假设是Ac2-DPD活性归因于酯基团的原位水解而释放的DPD。重要的是，与DPD相比，Ac2-DPD被证明是可以纯化和储存的稳定化合物。
• <i>S</i>-Ribosylhomocysteinase (LuxS) Is a Mononuclear Iron Protein
  作者：Jinge Zhu、Eric Dizin、Xubo Hu、Anne-Sophie Wavreille、Junguk Park、Dehua Pei

  DOI：10.1021/bi034289j

  日期：2003.4.1

  metal ion is Fe(2+). The electronic absorption spectrum of the Co(II)-substituted LuxS underwent dramatic catalysis-dependent changes, suggesting the direct involvement of the metal ion in catalysis. Site-directed mutagenesis studies showed that Glu-57 and Cys-84 are essential for catalysis, most likely acting as general acids/bases. Reaction in D(2)O resulted in the incorporation of deuterium at the C-1

  S-核糖基同型半胱氨酸酶（LuxS）催化S-核糖基同型半胱氨酸（SRH）的硫醚键的裂解，产生L-同型半胱氨酸和4,5-二羟基-2,3-戊二酮（DHPD）。这是革兰氏阳性和革兰氏阴性细菌中II型自诱导剂（AI-2）生物合成途径中的关键步骤。先前的研究表明，LuxS包含二价金属辅助因子，该因子已经被提议为Zn（2+）离子。为了深入了解这种异常反应的催化机理和金属辅因子的功能，我们开发了一种高效的表达和纯化系统，以生产富含Fe（2 +），Co（2+）或Zn（2+）的LuxS。 ）。金属取代的LuxS与天然酶的催化性能和稳定性的比较表明，天然金属离子是Fe（2+）。Co（II）取代的LuxS的电子吸收光谱经历了催化作用的剧烈变化，表明金属离子直接参与了催化作用。定点诱变研究表明，Glu-57和Cys-84是催化必不可少的，最有可能充当一般的酸/碱。D（2）O中的反应导致氘在二酮产物的C-1，C-2
• Quorum Sensing in Bacteria
  作者：Melissa B. Miller、Bonnie L. Bassler

  DOI：10.1146/annurev.micro.55.1.165

  日期：2001.10

  cell-cell communication via autoinducers occurs both within and between bacterial species. Furthermore, there is mounting data suggesting that bacterial autoinducers elicit specific responses from host organisms. Although the nature of the chemical signals, the signal relay mechanisms, and the target genes controlled by bacterial quorum sensing systems differ, in every case the ability to communicate with one

  群体感应是对基因表达的调节，以响应细胞种群密度的波动。群体感应细菌产生并释放称为自动诱导剂的化学信号分子，其浓度随着细胞密度的增加而增加。自动诱导剂的最小阈值刺激浓度的检测导致基因表达的改变。革兰氏阳性和革兰氏阴性细菌使用群体感应通信电路来调节各种生理活动。这些过程包括共生，毒力，能力，结合，抗生素产生，运动，孢子形成和生物膜形成。通常，革兰氏阴性细菌使用酰化的高丝氨酸内酯作为自体诱导剂，革兰氏阳性细菌使用加工的寡肽进行交流。该领域的最新进展表明，经由自动诱导剂的细胞-细胞通讯发生在细菌种类之内和之间。此外，越来越多的数据表明细菌自诱导物引起宿主生物体的特异性反应。尽管化学信号的性质，信号中继机制和由细菌群体感应系统控制的靶基因有所不同，但在每种情况下，彼此交流的能力使细菌能够协调细菌的基因表达，从而协调其行为。整个社区。据推测，该过程赋予细菌某些高级生物的特质。因此，细菌中群体感应系统的进化可能是多细胞性发展的早期步骤之一。