N-十二酰基-DL-高丝氨酸内酯(2-8°C) | 137173-46-7

• 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-十二酰基-DL-高丝氨酸内酯(2-8°C)
• 英文名称: N-dodecanoyl-DL-homoserine lactone
• 英文别名: N-(2-oxooxolan-3-yl)dodecanamide
• CAS: 137173-46-7；18627-38-8
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: WILLZMOKUUPJSL-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  485.8±34.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：10mg/mL； DMF：1mg/mL；二甲基亚砜：1mg/mL
• 保留指数：
  2384.8

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C，密封保存，并保持干燥。

制备方法与用途

生物活性

N-十二烷酰-L-羟基丁二酸乳酸酯（C12-HSL）是一种群体感应（QS）信号分子，可用于阻止群体感应并抑制铜绿假单胞菌（Pseudomonas aeruginosa）生物膜的形成。

体外研究

干扰细胞间的通信或群体感应（QS）被认为是一种减少细菌致病性和抗药性的有前景的方法。

反应信息

• 作为产物：
  描述：

  月桂酸 、 α-氨基-γ-丁内酯氢溴酸盐 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 反应 24.0h， 以71.5%的产率得到N-十二酰基-DL-高丝氨酸内酯(2-8°C)
  参考文献：
  名称：

  Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration

  摘要：

  The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

  DOI：

  10.1021/np900043j

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。
• MICROBIAL ACTIVITY IMPROVEMENT AGENT, MICROBIAL ACTIVITY IMPROVEMENT METHOD, AND BIOLOGICAL WASTE TREATMENT METHOD
  申请人：Sumitomo Heavy Industries, LTD.

  公开号：EP2447355A1

  公开（公告）日：2012-05-02

  A compound selected from the group consisting of 4-quinolone and derivatives thereof, homoserine lactone derivatives, and indole and derivatives thereof, and salts thereof have an action of a microbial activity improvement agent, and when it is used for a microbial activity improvement method and a biological waste treatment method, the compound or the salt thereof is useful to achieve the improvement in the treatment capacity that transcends the limit of improvement in the treatment capacity of conventional biological waste treatment facilities.

  选自 4-喹啉酮及其衍生物、均丝氨酸内酯衍生物和吲哚及其衍生物组成的组的化合物及其盐具有微生物活性改良剂的作用，当用于微生物活性改良方法和生物废物处理方法时，该化合物或其盐有助于实现处理能力的改良，超越传统生物废物处理设施处理能力的改良极限。
• Gene delivery carrier
  申请人：Massachusetts Institute of Technology

  公开号：US11041069B2

  公开（公告）日：2021-06-22

  Disclosed are methods, compositions, reagents, systems, and kits to prepare and utilize poly (β-amino ester) (PBAE) polymers, which are synthesized via Michael addition reactions of diacrylates and amines disclosed herein. Various embodiments utilize lactones and lactone derivatives to generate the diacrylate compounds. The PBAE polymers are shown to be effective biodegradable carriers for the delivery of an agent such as an organic molecule, inorganic molecule, nucleic acid, protein, peptide, polynucleotide, targeting agent, an isotopically labeled chemical compound, vaccine, or an immunological agent.

  本文公开了制备和利用聚（β-氨基酯）（PBAE）聚合物的方法、组合物、试剂、系统和试剂盒，这些聚合物是通过本文公开的二丙烯酸酯和胺的迈克尔加成反应合成的。不同的实施例利用内酯和内酯衍生物生成二丙烯酸酯化合物。事实证明，PBAE 聚合物是一种有效的可生物降解载体，可用于传递有机分子、无机分子、核酸、蛋白质、肽、多核苷酸、靶向剂、同位素标记的化合物、疫苗或免疫制剂等制剂。
• SYSTEMS AND METHODS FOR DIAGNOSIS AND MONITORING OF BACTERIA-RELATED CONDITIONS
  申请人：Daunert Sylvia

  公开号：US20100291566A1

  公开（公告）日：2010-11-18

  The presently-disclosed subject matter provides systems, methods, and kits for diagnosing and/or monitoring a bacteria-related condition of interest in a subject by providing a cell sensing system, each system containing a reporter molecule capable of detecting binding of a quorum sensing molecule and capable of generating a detectable signal.
• 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.