(R)-(+)-N-(3-oxo-tetradecanoyl)homoserine lactone | 1030851-89-8

• 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: (R)-(+)-N-(3-oxo-tetradecanoyl)homoserine lactone
• 英文别名: N-3-oxo-tetradecanoyl-L-homoserine lactone；N-3-oxo-myristoyl-L-homoserine lactone；(R)-(+)-N-(3-oxo-tetradecanoyl)-HSL；3-oxo-N-[(3R)-2-oxooxolan-3-yl]tetradecanamide
• CAS: 1030851-89-8
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: YQFJJDSGBAAUPW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (R)-(+)-alpha-氨基-gamma-丁内酯盐酸盐 、 2,2-dimethyl-4,6-dioxo-5-dodecanoyl-1,3-dioxane 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (R)-(+)-N-(3-oxo-tetradecanoyl)homoserine lactone
  参考文献：
  名称：

  Absolute Configuration and Antimicrobial Activity of Acylhomoserine Lactones

  摘要：

  (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.

  DOI：

  10.1021/np800127b

文献信息

• COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA
  申请人：BLACKWELL Helen E.

  公开号：US20100305182A1

  公开（公告）日：2010-12-02

  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.

  本发明提供了调节群体感应细菌的通讯和毒力的组合物和方法。在各种示例实施方案中，本发明提供了一种群体感应化合物的组合库，包括天然存在和非天然存在的酰基-同型半乳糖内酯（AHL）类似物的合成类似物，以及这些化合物的合成和使用方法。
• TRAIL ENHANCERS FOR THE SELECTIVE KILLING OF CANCER CELLS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20160272603A1

  公开（公告）日：2016-09-22

  The invention is directed to methods of inducing apoptosis, arresting cell cycle, or inhibiting cellular proliferation, or any combination thereof, in a tumor cell, by administration of an effective amount of an N-acyl homoserine lactone analog (AHL), optionally in conjunction with a tumor modulating agent such tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) to the patient. Novel bioactive analogs of an N-acyl homoserine lactone are also provided.
• US7642285B2
  申请人：——

  公开号：US7642285B2

  公开（公告）日：2010-01-05
• US8269024B2
  申请人：——

  公开号：US8269024B2

  公开（公告）日：2012-09-18
• US9604950B2
  申请人：——

  公开号：US9604950B2

  公开（公告）日：2017-03-28