N-（3-氧代辛酰基）-DL-高丝氨酸内酯（-20°C） | 106983-27-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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
• 中文名称: N-（3-氧代辛酰基）-DL-高丝氨酸内酯（-20°C）
• 中文别名: N-(3-氧代辛酰基)-DL-高丝氨酸内酯(-20°C)
• 英文名称: N-(3-oxooctanoyl)homoserine lactone
• 英文别名: N-(3-oxooctanoyl)-DL-homoserine lactone；3-oxo-N-(2-oxooxolan-3-yl)octanamide
• CAS: 106983-27-1
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: FXCMGCFNLNFLSH-UHFFFAOYSA-N

物化性质

• 溶解度：
  在氯仿的溶解度为50mg/mL，澄清，非常淡黄色

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

安全信息

• WGK Germany：
  3
• 海关编码：
  2932209090

制备方法与用途

生物活性

N-(3-氧化辛酰基)-DL-高丝氨酸内酯（N-(3-Oxooctanoyl)-DL-homoserine lactone）是由革兰氏阴性菌产生的一种 N-酰基高丝氨酸内酯 (AHL)，具有立体化学结构依赖性的植物根生长调节活性。

体外研究

S 对映体的 N-(3-氧化辛酰基)-DL-高丝氨酸内酯比 R 对映体更有效地促进糖 cane 的根部萌发。两种对映体（R 和 S）都能使根细胞伸长。

反应信息

• 作为反应物：
  描述：

  N-（3-氧代辛酰基）-DL-高丝氨酸内酯（-20°C） 在 Calibrin Z 作用下， 反应 0.5h， 生成 2-庚酮 、 γ-丁内酯 、 3-氨基四氢呋喃-2-酮氢溴酸盐 、 3-oxooctanamide 、 3-oxo-octanal
  参考文献：
  名称：

  黏土材料对哈维氏弧菌的群体感应破坏

  摘要：

  这项工作描述了使用粘土矿物的作为催化剂用于群体感应分子的降解ñ - （3- oxooctanoyl） - DL高丝氨酸内酯。某些粘土矿物由于其表面性质和孔隙率而可以催化将群体感应分子降解为较小的碎片。还通过监测细菌的发光和种群密度，研究了生长的革兰氏阴性哈维氏弧菌细菌培养物中对群体感应的破坏，其中通过减少发光观察了细菌群体感应活性的淬灭。这项研究的结果表明，食品级粘土可用作破坏各种介质中细菌活性的生物催化剂。

  DOI：

  10.1021/acs.jafc.7b03918
• 作为产物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 、 5-hexanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 N-（3-氧代辛酰基）-DL-高丝氨酸内酯（-20°C）
  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。
• APPLICATION OF POROUS MATERIALS FOR BACTERIAL QUORUM SENSING INHIBITION/DISRUPTION
  申请人：Oil-Dri Corporation of America

  公开号：EP3423562A1

  公开（公告）日：2019-01-09
• Methods of treating or preventing an infectious disease using an immunogenic conjugate of a gram-negative bacterial autoinducer molecule or antibodies that immunospecifically bind a gram-negative bacterial autoinducer molecule
  申请人：Kende S. Andrew

  公开号：US20070231839A1

  公开（公告）日：2007-10-04

  The present invention relates to an immunogenic conjugate comprising a carrier molecule coupled to an autoinducer of a Gram negative bacteria The immunogenic conjugate, when combined with a pharmaceutically acceptable carrier, forms a suitable vaccine for mammals to prevent infection by the Gram negative bacteria The immunogenic conjugate is also used to raise and subsequently isolate antibodies or binding portions thereof which are capable of recognizing and binding to the autoinducer. The antibodies or binding portions thereof are utilized in a method of treating infections, a method of inhibiting autoinducer activity, and in diagnostic assays which detect the presence of autoinducers or autoinducer antagonists in fluid or tissue samples. TABLE OF CONTENTS Page 1. FIELD OF THE INVENTION 1 2. BACKGROUND OF THE INVENTION 1 3. SUMMARY OF THE INVENTION 4 4. BRIEF DESCRIPTION OF THE DRAWINGS 7 5. DETAILED DESCRIPTION OF THE INVENTION 7 5.1 Isolation and Synthesis of Homoserine Lactones 7 5.2 Bacterial Autoinducer Conjugation to a Carrier 17 5.3 Generation of Antibodies to BAI Immunogenic conjugates 19 5.4 Therapeutic Uses of Immunogenic conjugates 22 or Antibodies Thereto 5.4.1 Administration and Formulation 22 5.4.2 Effective Dose 25 5.5 Diagnostic Methods 27 6. EXAMPLE: SYNTHESIS 32 Preparation of Compound C 32 Preparation of Compound D 32 Preparation of Compound 5 32 Preparation of Compound 6 33 Preparation of Compound 7 33 Preparation of Compound 8 33 Preparation of Compound 10 34 Preparation of Compound 11 34 Preparation of Compound 13 35 Preparation of Compound 12 35 Preparation of Compound 14 35 Preparation of Compound 15 36 Preparation of Compound 17 36 Preparation of Compound 21 37 Preparation of Compound 22 37 Preparation of Compound 24 38 Preparation of Compound 25 38 Preparation of Compound 27 38 Preparation of Compound 29 39 7. EXAMPLE: PRODUCTION OF BAI ANTIBODIES 39 7.1 PAI'S Role In Virulence 39 7.2 Anti-PAI Polyclonal Antibodies 40 7.3 Neutralization of PAI With Antibodies 40
• ACYL-HOMOSERINE LACTONE DERIVATIVES FOR IMPROVING PLANT YIELD
  申请人：Dahmen Peter

  公开号：US20140221210A1

  公开（公告）日：2014-08-07

  The present invention relates to methods for improving crop yield, chlorophyll content, seed germination, nutrient uptake or mycorrhizal symbiotic interaction of a plant, comprising the use of acyl-homoserine lactone derivatives and to composition comprising said derivatives of formula (I) or (II) wherein R1 is hydrogen or hydroxyl; R2 is a saturated or mono-unsaturated linear aliphatic group comprising 1 to 15 atoms.
• US7384639B2
  申请人：——

  公开号：US7384639B2

  公开（公告）日：2008-06-10