N-(3-oxooctanoyl)-D-homoserine lactone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3-oxooctanoyl)-D-homoserine lactone
• 英文别名: (R)-N-(3-oxooctanoyl)homoserine lactone；N-(3-oxooctanoyl)-L-homoserine lactone；N-(β-ketooctanoyl)-L-homoserine；(R)-(+)-N-(3-oxo-octanoyl)-HSL；(R)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)octanamide；3-oxo-N-[(3R)-2-oxooxolan-3-yl]octanamide
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: FXCMGCFNLNFLSH-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氧代辛酸 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 N-(3-oxooctanoyl)-D-homoserine lactone
  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

• 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。
• Acyl-homoserine Lactone from <i>Saccharum × officinarum</i> with Stereochemistry-Dependent Growth Regulatory Activity
  作者：Vanessa G. A. Olher、Nagela P. Ferreira、Alan G. Souza、Lucas U. R. Chiavelli、Aline F. Teixeira、Wanderley D. Santos、Silvana M. O. Santin、Osvaldo Ferrarese Filho、Cleuza C. Silva、Armando M. Pomini

  DOI：10.1021/acs.jnatprod.5b01075

  日期：2016.5.27

  could not be determined, both R and S enantiomers of N-(3-oxo-octanoyl)homoserine lactone were synthesized and tested in sugar cane culms. The enantiomers caused changes in the mass and length of buds and roots when used at micromolar concentrations. Using the sugar cane RB96-6928 variety, the S enantiomer increased sprouting of roots more effectively than the R enantiomer. Furthermore, scanning electron

  酰基高丝氨酸内酯（AHL）是革兰氏阴性细菌产生的一类化合物，用于化学通讯过程中，称为群体感应。关于细菌如何使用这些化合物来控制重要因子的表达，人们已经知道很多。但是，关于植物中AHL的存在及其作用的报道很少。在这项研究中，对甘蔗（Saccharum×officinarum）的叶子和茎的植物化学研究导致了N-（3-氧代-辛酰基）高丝氨酸内酯的鉴定。由于无法确定天然产物的绝对构型，因此N的R和S对映异构体合成了-（3-氧-辛酰基）高丝氨酸内酯，并在甘蔗茎中进行了测试。当以微摩尔浓度使用时，对映异构体引起芽和根的质量和长度的变化。与R对映异构体相比，使用甘蔗RB96-6928品种，S对映异构体更有效地增加了根部的发芽。此外，扫描电子显微镜显示与对照相比，R和S对映异构体均导致更多的拉伸根细胞。
• Use of acyl-homoserine lactone derivatives as anti-thrombotic agents
  申请人：The University of Toledo

  公开号：US10195177B2

  公开（公告）日：2019-02-05

  Uses of acyl-homoserine lactone compounds are described. In particular, uses of acyl-homoserine lactone compounds as anti-thrombotic agents, to inhibit platelets from becoming hypersensitive, and/or to prevent thrombosis, are described.

  描述了酰基高丝氨酸内酯化合物的用途。特别是描述了酰基高丝氨酸内酯化合物作为抗血栓药、抑制血小板变得超敏和/或防止血栓形成的用途。
• Absolute Configuration and Antimicrobial Activity of Acylhomoserine Lactones
  作者：Armando M. Pomini、Anita J. Marsaioli

  DOI：10.1021/np800127b

  日期：2008.6.1

  (S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano is reported herein. As with all other substances of this class, the lactone moiety possesses S configuration, corroborating the hypothesis that it shares the same biosynthetic pathway as the (S)-N-hexanoylhomoserine lactone and also that some LuxI homologues can accept both hexanoyl- and heptanoyl-ACP as precursors. Evaluation of the antimicrobial activity of enantiomeric acylhomoserine lactones against three Gram-positive bacteria (Bacillus cereus, B. subtilis, and Staphylococcus aureus) revealed important features between absolute configuration and antimicrobial activity. The N-heptanoylhomoserine lactone was considerably less active than the 3-oxo derivatives. Surprisingly, non-natural (R)-N-(3-oxo-octanoyl)homoserine lactone was as active as the S enantiomer against B. cereus, while the synthetic racemic product was less active than either enantiomer.
• Modulation of Bacterial Quorum Sensing with Synthetic Ligands
  申请人：Blackwell Helen E.

  公开号：US20080312319A1

  公开（公告）日：2008-12-18

  The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.