N-hexanoyl-L-homoserine | 1043897-54-6

• 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-hexanoyl-L-homoserine
• 英文别名: N-hexanoyl-L-homoserinelactone；HHS；(2S)-2-(hexanoylamino)-4-hydroxybutanoic acid
• CAS: 1043897-54-6
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: BJLILZXVIKTHKQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正己基-L-高丝氨酸内酯 在 N-acylhomoserine lactonase YS-8 from Geobacillus caldoxylosilyticus, thermophilic bacterium from volcanic soil in Indonesia 作用下， 生成 N-hexanoyl-L-homoserine
  参考文献：
  名称：

  Isolation and Characterization ofN-Acylhomoserine Lactonase from the Thermophilic Bacterium,Geobacillus caldoxylosilyticusYS-8

  摘要：

  从印度尼西亚火山土壤中分离出的嗜热硅化细菌YS-8能够降解各种长度和酰基侧链取代的N-酰基高丝氨酸内酯（AHL），降解温度范围为30-70℃。纯化的AHL降解酶显示为32 kDa的单条带，其N端氨基酸序列确定为ANVIKARPKLYVMDN，初步表明AHL降解酶是AHL内酯酶。纯化酶的AHL降解活性在pH 7.5和50℃时达到最大，即使在60℃下热处理3小时后仍能保持约50%的活性，表现出与热稳定酶一致的性质。质谱分析表明，AHL降解酶通过水解内酯，作为AHL内酯酶催化N-3-氧代己酰-L-高丝氨酸内酯和N-己酰-L-高丝氨酸内酯的环状内酯开环。

  DOI：

  10.1271/bbb.110322

文献信息

• Cell-free expression system for the detection of bacterial biofilms
  申请人：Freemont Paul

  公开号：US20100021942A1

  公开（公告）日：2010-01-28

  Provided is a cell-free expression system and method for its use for detecting the presence of a bacterial biofilm on a surface, wherein the film comprises a) an exogenous quorum sensing protein or an exogenous nucleic acid sequence coding for a quorum sensing protein capable of selectively binding to a bacterial signaling molecule; and b) an exogenous nucleic acid sequence comprising a promoter operably linked to a nucleic acid sequence coding for a marker protein, wherein the promoter is regulated by the binding of the quorum sensing protein to the bacterial signaling molecule. Further provided is an aerosol formulation, as well as an adhesive bandage, each of which may be used for detecting the presence of a bacterial biofilm on a surface, comprising the disclosed cell free expression system and methods therefor.

  提供了一种无细胞表达系统及其使用方法，用于检测表面上细菌生物膜的存在，其中膜包括a）外源性定量感应蛋白或编码定量感应蛋白的外源性核酸序列，其能够选择性地结合到细菌信号分子；以及b）包括可操作地连接到编码标记蛋白的核酸序列的启动子的外源性核酸序列，其中启动子由定量感应蛋白与细菌信号分子的结合调节。此外，还提供了气雾剂配方以及粘合绷带，每种都可以用于检测表面上的细菌生物膜，包括所述的无细胞表达系统及其方法。
• Abiotic Hydrolysis Kinetics of<i>N</i>-Acyl-L-homoserine Lactones: Natural Silencing of Bacterial Quorum Sensing Signals
  作者：Eric W. Ziegler、Alan B. Brown、Nasri Nesnas、Andrew G. Palmer

  DOI：10.1002/ejoc.201900322

  日期：2019.5.8

  Gram‐negative bacteria utilize N‐acyl‐L‐homoserine lactones (AHLs) to coordinate gene expression in a population‐density dependent manner. These molecules undergo hydrolysis at pH ≥ 7. In this study, we measure the hydrolysis rate of various AHLs at fixed alkalinities and determine the species' half‐lives using proton NMR. Our findings underscore the role that the environment plays in this phenomenon

  革兰氏阴性细菌利用N-酰基-L-高丝氨酸内酯（AHL）来以种群密度依赖性的方式协调基因表达。这些分子在pH≥7时会发生水解。在这项研究中，我们测量了固定碱度下各种AHL的水解速率，并使用质子NMR确定了该物种的半衰期。我们的发现强调了环境在这种现象中的作用，并将有助于制定策略来控制细菌中的此类行为。
• Autoinducer synthase modulating compounds and uses therefor
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：EP1834645A1

  公开（公告）日：2007-09-19

  Provided are compositions and methods useful for modulating the activity of autoinducer synthase catalysts. A method for identifying modulators of the autoinducers synthesis reaction is also provided. Such modulators are useful for controlling bacterial growth and can be used for therapeutic treatment of bacterial infections particularly in immunocompromised subjects. They are also useful in treating disease states associated with autoinducer synthesis and biofilm development.

  本文提供了用于调节自体诱导剂合成酶催化剂活性的组合物和方法。还提供了一种确定自身诱导剂合成反应调节剂的方法。这种调节剂可用于控制细菌生长，并可用于细菌感染的治疗，特别是免疫力低下者。它们还可用于治疗与自身诱导剂合成和生物膜发展相关的疾病状态。
• PEPTIDE WITH QUORUM-SENSING INHIBITORY ACTIVITY, POLYNUCLEOTIDE THAT ENCODES SAID PEPTIDE, AND THE USES THEREOF
  申请人：Universidade de Santiago de Compostela

  公开号：EP3020814A1

  公开（公告）日：2016-05-18

  The invention relates to the cloning, sequencing and characterization of the gene responsible for Quorum Quenching (QQ) activity against Quorum Sensing (QS) signals of the Tenacibaculum sp. strain 20J (CECT7426). Said gene encodes a peptide having at least lactonase activity with a percentage of identity less than 38% with the lactonases described up until now for other species, as well as the sequences of the homologous genes present in other species of the genus Tenacibaculum. Said peptide shows a broad spectrum of activity degrading optionally substituted N-acyl-homoserine lactones (AHLs) of 4-14 carbon atoms in the side chain thereof, is active at pH comprised between 3 and 9, proteinase K- and chymotrypsin-resistant and does not interact with β-lactam antibiotics.

  本发明涉及到负责对Tenacibaculum sp.菌株20J（CECT7426）的法定人数感应（QS）信号进行法定人数淬灭（QQ）活性的基因的克隆、测序和鉴定。该基因编码的肽至少具有内酯酶活性，与迄今为止其他物种的内酯酶以及天牛属其他物种的同源基因序列的相同度低于 38%。所述肽具有广谱活性，能降解侧链中含有 4-14 个碳原子的任选取代的 N-酰基高丝氨酸内酯（AHL），在 pH 值介于 3 和 9 之间时具有活性，抗蛋白酶 K 和糜蛋白酶，并且不与β-内酰胺类抗生素相互作用。
• A Phenylalanine Clamp Controls Substrate Specificity in the Quorum-Quenching Metallo-γ-lactonase from <i>Bacillus thuringiensis</i>
  作者：Ce Feng Liu、Dali Liu、Jessica Momb、Pei W. Thomas、Ashley Lajoie、Gregory A. Petsko、Walter Fast、Dagmar Ringe

  DOI：10.1021/bi400050j

  日期：2013.3.5

  Autoinducer inactivator A (AiiA) is a metal-dependent N-acyl homoserine lactone hydrolase that displays broad substrate specificity but shows a preference for substrates with long N-acyl substitutions. Previously, crystal structures of AiiA in complex with the ring-opened product N-hexanoyl-L-homoserine revealed binding interactions near the metal center but did not identify a binding pocket for the N-acyl chains of longer substrates. Here we report the crystal structure of an AiiA mutant, F107W, determined in the presence and absence of N-decanoyl-L-homoserine. F107 is located in a hydrophobic cavity adjacent to the previously identified ligand binding pocket, and the F107W mutation results in the formation of an unexpected interaction with the ring-opened product. Notably, the structure reveals a previously unidentified hydrophobic binding pocket for the substrate's N-acyl chain. Two aromatic residues, F64 and F68, form a hydrophobic clamp, centered around the seventh carbon in the product-bound structure's decanoyl chain, making an interaction that would also be available for longer substrates, but not for shorter substrates. Steady-state kinetics using substrates of various lengths with AiiA bearing mutations at the hydrophobic clamp, including insertion of a redox-sensitive cysteine pair, confirms the importance of this hydrophobic feature for substrate preference. Identifying the specificity determinants of AiiA will aid the development of more selective quorum-quenching enzymes as tools and as potential therapeutics.