(S)-2-((5-(dimethylamino)naphthalene)-1-sulfonamido)-N-(2-oxotetrahydrofuran-3-yl)acetamide | 1061590-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-((5-(dimethylamino)naphthalene)-1-sulfonamido)-N-(2-oxotetrahydrofuran-3-yl)acetamide
• 英文别名: 2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-N-[(3S)-2-oxooxolan-3-yl]acetamide
• CAS: 1061590-41-7
• 化学式: C₁₈H₂₁N₃O₅S
• 分子量: 391.448
• InChiKey: SELUSYJNNVIITK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丹酰氯 、 高丝氨酸内酯氢溴酸盐 、 聚甘氨酸 在 碳酸氢钠 、 三乙胺 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (S)-2-((5-(dimethylamino)naphthalene)-1-sulfonamido)-N-(2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  Autoinducer-fluorophore conjugates enable FRET in LuxR proteins in vitro and in cells

  摘要：

  在许多革兰氏阴性细菌中，细胞间信号传导或称群体感应（QS）由小分子信号（N-酰基-L-高丝氨酸内酯，AHL）及其同源受体（LuxR型蛋白）控制。由于分离和操纵大多数LuxR型蛋白存在困难，这些细菌中QS的机制基础受到严重限制。有关LuxR型蛋白定量直接结合实验的报告很少，能够提供此类数据的可靠且可推广的方法基本不存在。我们在此报告了一种福斯特共振能量转移（FRET）检测方法，该方法利用了（1）位于LuxR型蛋白配体结合位点的保守色氨酸和合成荧光团-AHL结合物，以及（2）分离与弱激动剂结合的蛋白。FRET检测方法可以直接测量配体与受体结合的亲和力——无论是在体外还是在细胞内——并且已证明与六种LuxR型蛋白兼容。这些方法将推进对LuxR型蛋白机制的基础研究以及小分子QS调节剂的开发。使用细菌群体感应LuxR型蛋白的保守色氨酸和合成荧光团-酰基-高丝氨酸内酯结合物的基于FRET的检测方法能够测量配体结合的亲和力，无论是在体外还是在细胞内。

  DOI：

  10.1038/s41589-022-01089-1

文献信息

• Modulation of Bacterial Quorum Sensing With Synthetic Ligands
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20200115356A1

  公开（公告）日：2020-04-16

  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.
• MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20220411390A1

  公开（公告）日：2022-12-29

  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.
• US9796694B2
  申请人：——

  公开号：US9796694B2

  公开（公告）日：2017-10-24