N-pentanoyl-(S)-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-pentanoyl-(S)-homoserine lactone
• 英文别名: N-Pentanoyl-L-homoserine lactone；N-[(3S)-2-oxooxolan-3-yl]pentanamide
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: BFIMURGDHGARTN-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-pentanoyl-(S)-homoserine lactone 在 Bacillus thuringiensis N-acyl homoserine lactone hydrolase 、 水 、 sodium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 生成 N-pentanoylhomoserine
  参考文献：
  名称：

  A Phenylalanine Clamp Controls Substrate Specificity in the Quorum-Quenching Metallo-γ-lactonase from Bacillus thuringiensis

  摘要：

  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.

  DOI：

  10.1021/bi400050j
• 作为产物：
  描述：

  4-戊烯酰氯 在 硼氘化钠 、 palladium on activated charcoal 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 N-pentanoyl-(S)-homoserine lactone
  参考文献：
  名称：

  N-酰基-L-高丝氨酸内酯 (AHL) 的氘和氚标记通过逐层法中的双键催化还原

  摘要：

  N-酰基-L-高丝氨酸内酯 (AHL) 是在革兰氏阴性细菌中发现的信号分子，使细菌能够通过群体感应相互交流，并通过跨界信号与它们的真核宿主细胞进行交流。对跨界信号机制知之甚少。合成了氘和氚标记的 AHL，以检测细胞分布并监测 AHL 的膜转运。大多数氚标记方法使用氚气，这很难处理，但是，在这里我们提出了一种新的无气体方法，通过双键的催化还原获得氘和氚标记的末端不饱和 AHL。这种罕见的双键还原使用硼氢化钠-[2H] 或硼氢化钠-[3H]，并在乙酸钯 (II) 存在下进行，乙酸钯 (II) 在独特的逐层系统中充当催化剂。此外，还提供了对所得同位素体的详细核磁共振分析。

  DOI：

  10.1002/ejoc.201300084

文献信息

• [EN] SYNTHETIC LIGANDS THAT MODULATE THE ACTIVITY OF THE RHLR QUORUM SENSING RECEPTOR<br/>[FR] LIGANDS SYNTHÉTIQUES MODULANT L'ACTIVITÉ DU RÉCEPTEUR DE DÉTECTION DU QUORUM RHLR
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2017190116A1

  公开（公告）日：2017-11-02

  RhlR modulators including agonist and antagonists which are useful for modulating QS phenotypes in Gram-negative bacteria. Certain compounds of general formula A-W-HG having various carbocyclic ad heterocyclic head groups (HG) and various tail groups (A), where -W- is -CO-NH-, -SO2-NH-, -CO-NH-CH2-, or -SO2-NH-CH2- are RhlR agonists or antagonists. The compounds are useful in methods of modulating quorum sensing in Gram-negative bacteria, particularly in Pseudomonas. Compositions including certain RhlR modulators are useful for decreasing the virulence of Gram-negative bacteria. Pharmaceutical compositions comprising certain RhlR modulators are useful for treatment of infections of Gram-negative bacteria.

  RhlR调节剂包括激动剂和拮抗剂，对调节革兰氏阴性细菌中的QS表型有用。具有一般公式A-W-HG的某些化合物具有各种碳环和杂环头基团（HG）和各种尾基团（A），其中-W-为-CO-NH-，-SO2-NH-，-CO-NH-CH2-或-SO2-NH-CH2-是RhlR激动剂或拮抗剂。这些化合物在调节革兰氏阴性细菌中的群体感应方法中有用，特别是在铜绿假单胞菌中。包含某些RhlR调节剂的组合物有助于降低革兰氏阴性细菌的毒力。包含某些RhlR调节剂的药物组合物有助于治疗革兰氏阴性细菌感染。
• Synthetic ligands that modulate the activity of the RhlR quorum sensing receptor
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11247976B2

  公开（公告）日：2022-02-15

  RhlR modulators including agonist and antagonists which are useful for modulating QS phenotypes in Gram-negative bacteria. Certain compounds of general formula A-W-HG having various carbocyclic ad heterocyclic head groups (HG) and various tail groups (A), where —W— is —CO—NH—, —SO2—NH—, —CO—NH—CH2—, or —SO2—NH—CH2— are RhlR agonists or antagonists. The compounds are useful in methods of modulating quorum sensing in Gram-negative bacteria, particularly in Pseudomonas. Compositions including certain RhlR modulators are useful for decreasing the virulence of Gram-negative bacteria. Pharmaceutical compositions comprising certain RhlR modulators are useful for treatment of infections of Gram-negative bacteria.

  RhlR 调节剂，包括激动剂和拮抗剂，可用于调节革兰氏阴性细菌的 QS 表型。通式 A-W-HG 的某些化合物具有各种碳环或杂环头基 (HG) 和各种尾基 (A)，其中 -W- 是 -CO-NH-、-SO2-NH-、-CO-NH-CH2- 或 -SO2-NH-CH2- 是 RhlR 激动剂或拮抗剂。这些化合物可用于调节革兰氏阴性细菌，特别是假单胞菌的法定量感应。包括某些 RhlR 调节剂的组合物有助于降低革兰氏阴性细菌的毒力。包含某些 RhlR 调节剂的药物组合物可用于治疗革兰氏阴性细菌感染。
• Autoinducer compounds and their uses
  申请人：——

  公开号：US20040115245A1

  公开（公告）日：2004-06-17

  The present invention discloses the autoinducer compounds, such as acyl homoserine lactones, acyl homocysteine lactone, acyl thiolactones, furanones or signal peptides, and their use in animal feed additives and animal feeds to improve animal performance.

  本发明公开了自体诱导剂化合物，如酰基高丝氨酸内酯、酰基高半胱氨酸内酯、酰基硫内酯、呋喃酮或信号肽，以及它们在动物饲料添加剂和动物饲料中的用途，以提高动物的生产性能。
• AUTOINDUCER COMPOUNDS AND THEIR USES
  申请人：Gormar Marketing Limited

  公开号：EP1361801A1

  公开（公告）日：2003-11-19
• Synthetic Ligands that Modulate the Activity of the RhlR Quorum Sensing Receptor
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20190144407A1

  公开（公告）日：2019-05-16

  RhlR modulators including agonist and antagonists which are useful for modulating QS phenotypes in Gram-negative bacteria. Certain compounds of general formula A-W-HG having various carbocyclic ad heterocyclic head groups (HG) and various tail groups (A), where —W— is —CO—NH—, —SO 2 —NH—, —CO—NH—CH 2 —, or —SO 2 —NH—CH 2 — are RhlR agonists or antagonists. The compounds are useful in methods of modulating quorum sensing in Gram-negative bacteria, particularly in Pseudomonas . Compositions including certain RhlR modulators are useful for decreasing the virulence of Gram-negative bacteria. Pharmaceutical compositions comprising certain RhlR modulators are useful for treatment of infections of Gram-negative bacteria.