2-(2-propyl-1,3-dioxolan-2-yl)acetic acid | 5735-99-9

• 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: 2-(2-propyl-1,3-dioxolan-2-yl)acetic acid
• 英文别名: 3,3-ethylene glycosyl hexanoyl acid；3,3-ethyleneglycosyl hexanoic acid；3,3-ethylenedioxo-hexanoic acid
• CAS: 5735-99-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: MNOZBVQGZXOGRT-UHFFFAOYSA-N

物化性质

• 沸点：
  292.0±15.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-propyl-1,3-dioxolan-2-yl)acetic acid 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 N-(3-hydroxypyridine-2-yl)-3-oxohexanoylamide
  参考文献：
  名称：

  EP2077109

  摘要：

  公开号：
• 作为产物：
  描述：

  3-oxocaproic acid 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 30.5h， 生成 2-(2-propyl-1,3-dioxolan-2-yl)acetic acid
  参考文献：
  名称：

  细菌群体感应和生物膜形成的小分子抑制剂

  摘要：

  细菌在称为群体感应的过程中使用小分子（或自诱导剂）监测其局部种群密度。在这里，我们报告了一种新的、有效的天然细菌自体诱导剂 [N-酰基 l-高丝氨酸内酯 (AHL)] 的合成途径，该途径易于合成类似物。该路线已应用于非天然 AHL 库的首次合成。在细菌报告基因和生物膜测定中对这些化合物的评估揭示了一组有效的群体感应拮抗剂。这些配体将作为有价值的新工具来探索群体感应在细菌发病机制中的作用。

  DOI：

  10.1021/ja0530321

文献信息

• Discovery of a quorum sensing modulator pharmacophore by 3D small-molecule microarray screening
  作者：David M. Marsden、Rebecca L. Nicholson、Mette E. Skindersoe、Warren R. J. D. Galloway、Hannah F. Sore、Michael Givskov、George P. C. Salmond、Mark Ladlow、Martin Welch、David R. Spring

  DOI：10.1039/c0ob00300j

  日期：——

  The screening of large arrays of drug-like small-molecules was traditionally a time consuming and resource intensive task. New methodology developed within our laboratories provides an attractive low cost, 3D microarray-assisted screening platform that could be used to rapidly assay thousands of compounds. As a proof-of-principle the platform was exploited to screen a number of quorum sensing analogs. Quorum sensing is used by bacterium to initiate and spread infection; in this context its modulation may have significant clinical value. 3D microarray slides were probed with fluorescently labeled ligand-binding domains of the LuxR homolog CarR from Erwinia carotovora subsp. carotovora. The 3D microarray platform was used to discover the biologically active chloro-pyridine pharmacophore, which was validated using a fluorometric ligand binding assay and ITC. Analogs containing the chloro-pyridine pharmacophore were found to be potent inhibitors of N-acyl-homoserine-lactone (AHL) mediated quorum sensing phenotypes in Serratia (IC50 = ∼5 μM) and Pseudomonas aeruginosa (IC50 = 10–20 μM).

  筛选大量类药物小分子的工作传统上是一个耗时且资源密集的任务。在我们的实验室中开发的新方法提供了一种经济划算的3D微阵列辅助筛选平台，可以快速检测成千上万的化合物。作为原理验证，该平台被用来筛选多种群体感应类似物。群体感应是细菌用来启动和传播感染的机制；在这个背景下，调节它可能具有重要的临床价值。3D微阵列载片使用了来自土壤腐生菌Erwinia carotovora subsp. carotovora的LuxR同源物CarR的荧光标记配体结合结构域进行探测。该3D微阵列平台用于发现生物活性的氯吡啶药效团，并通过荧光配体结合测定和等温量热法（ITC）进行了验证。含有氯吡啶药效团的类似物被发现能够有效抑制Serratia（IC50 ≈ 5 μM）和铜绿假单胞菌（Pseudomonas aeruginosa）（IC50 = 10–20 μM）中N-酰基同源肉桂酸内酯（AHL）介导的群体感应表型。
• AMIDE COMPOUND AND BACTERIAL DISEASE CONTROL AGENT FOR AGRICULTURAL AND HORTICULTURAL USE
  申请人：The University of Tokyo

  公开号：EP2221293A1

  公开（公告）日：2010-08-25

  The present invention provides an amide compound having antibacterial activity, and a bacterial infection control agent for agricultural and horticultural use that contains the amide compound. The novel amide compound of the present invention is represented by General Formula (1): wherein R is a -CH(R1)(R2) or a -CO(R2) group, R1 is a hydrogen atom or a hydroxyl group, and R2 is a C1-12 alkyl group.

  本发明提供一种具有抗菌活性的酰胺化合物，以及一种用于农业和园艺的细菌感染控制剂，其含有该酰胺化合物。本发明的新型酰胺化合物由通式（1）表示：其中R是一个-CH(R1)(R2)或一个-CO(R2)基团，R1是一个氢原子或一个羟基，R2是一个C1-12烷基基团。
• Detection and Quantitation of Bacterial Acylhomoserine Lactone Quorum Sensing Molecules via Liquid Chromatography–Isotope Dilution Tandem Mass Spectrometry
  作者：Amanda L. May、Mary E. Eisenhauer、Kristen S. Coulston、Shawn R. Campagna

  DOI：10.1021/ac202636d

  日期：2012.2.7

  A range of acylhomoserine lactones (AHLs) are used as intraspecies quorum sensing signals by Gram-negative bacteria, and the detection and quantitation of these molecules is of interest. This manuscript reports a liquid chromatographic–isotope dilution tandem mass spectrometric method for the quantitation of these molecules. A divergent solid-phase synthesis of stable-isotope-labeled AHLs suitable for use as an internal standard is reported. This route relies on the biomimetic conversion of a dideuterated methionine equivalent, N-Fmoc-(4,4-2H2)methionine, to the desired labeled AHL, and a representative series of eight of these molecules was produced in >95% purity and yields up to ∼50%. The representative AHL internal standards were then used to develop an optimized liquid chromatography—tandem mass spectrometric (LC–MS/MS) separation and detection protocol for these molecules, which relies on a high-efficiency C18 core–shell column to minimize the time necessary for separation. The addition of internal standards at different steps during sampling was also found to affect the analysis for hydrophobic AHLs with addition prior to cell removal giving the most accurate results. Taken together, the use of the internal standards and separation method reported herein provides a rapid and quantitative method for the study of AHL production in bacteria.

  一系列酰基高丝氨酸内酯（AHLs）作为革兰氏阴性菌的种内群体感应信号分子，对这些分子的检测和定量研究具有重要意义。本文报道了一种液相色谱-同位素稀释串联质谱法用于这些分子的定量分析。文中还报道了一种固相合成适合作内标物的稳定同位素标记AHLs的方法。该合成路线依赖于生物模拟转化二氘代甲硫氨酸类似物N-Fmoc-(4,4-2H2)甲硫氨酸至所需标记AHL的过程。我们成功制备了八个代表性分子，纯度>95%，产率高达约50%。然后，使用这些代表性AHL内部标准物，开发了一套优化的液相色谱-串联质谱（LC-MS/MS）分离与检测方案，该方案依赖于高效C18核壳柱以最小化分离所需时间。在采样过程中不同步骤添加内标物对疏水性AHL分析的影响也得到了研究，发现在细胞去除前添加内标物可获得最准确的结果。综上所述，本文报道的内标物和分离方法提供了一种快速且定量的方法用于研究细菌中AHL的产生。
• COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA
  申请人：Blackwell E. Helen

  公开号：US20060178430A1

  公开（公告）日：2006-08-10

  The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.

  本发明提供了用于调节群体感应细菌的通讯和毒性的组合物和方法。在各种示例实施方式中，该发明提供了一种群体感应化合物的组合库，包括天然发生和非天然发生的酰基-同型半胱氨酸内酯（AHL）类似物的合成类似物，以及合成和使用这些化合物的方法。
• Synthesis of a Biotin-Labeled Quorum-Sensing Molecule: Towards a General Method for Target Identification
  作者：David Spring、Richard Spandl、Rebecca Nicholson、David Marsden、James Hodgkinson、Xianbin Su、Gemma Thomas、George Salmond、Martin Welch

  DOI：10.1055/s-2008-1077978

  日期：2008.8

  The synthesis of bacterial quorum-sensing regulator N-(3-oxohexanoyl)-l-homoserine lactone (OHHL) and biotin-tagged OHHL is reported. The latter will be applied to developing a general method to address the ‘target identification problem’ in chemical genetics.

  报道了细菌群体感应调节剂 N-(3-氧代己酰基)-l-高丝氨酸内酯 (OHHL) 和生物素标记的 OHHL 的合成。后者将用于开发解决化学遗传学中“目标识别问题”的通用方法。