(S)-N-3-hydroxy-(7Z)-tetradecenoyl-homoserine lactone | 273734-65-9

• 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: (S)-N-3-hydroxy-(7Z)-tetradecenoyl-homoserine lactone
• 英文别名: (S)-N-3-hydroxy-(7Z)-tetradecenoyl-HSL；N-(3-Hydroxy-7-cis-tetradecenoyl)homoserine lactone；(Z)-3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]tetradec-7-enamide
• CAS: 273734-65-9
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: GFSFGXWHLLUVRK-UPVLWJCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-3-hydroxy-(7Z)-tetradecenoyl-homoserine lactone 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-N-3-mesyl-(7Z)-tetradecenoyl-homoserine lactone
  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
• 作为产物：
  描述：

  (S)-3-oxo-(7Z)-tetradecenoyl-homoserine lactone 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 以88%的产率得到(S)-N-3-hydroxy-(7Z)-tetradecenoyl-homoserine lactone
  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

• Device including altered microorganisms, and methods and systems of use
  申请人：Amodei Dario G.

  公开号：US20110027181A1

  公开（公告）日：2011-02-03

  Devices, methods, and systems are described for administration to at least one biological tissue of at least one device including at least one altered microorganism. In an embodiment, the altered microorganism includes at least one nucleic acid construct encoding at least one therapeutic agent.
• US8682619B2
  申请人：——

  公开号：US8682619B2

  公开（公告）日：2014-03-25
• US8734823B2
  申请人：——

  公开号：US8734823B2

  公开（公告）日：2014-05-27
• [EN] STRUCTURAL BASIS OF QUORUM SENSING SIGNAL GENERATION AND METHODS AND THERAPEUTIC AGENTS DERIVED THEREFROM<br/>[FR] BASE STRUCTURALE DE GENERATION DE SIGNAUX DE DETECTION DE QUORUM ET METHODES ET AGENTS THERAPEUTIQUES DERIVES RESULTANTS
  申请人：UNIV COLORADO STATE

  公开号：WO2003064588A2

  公开（公告）日：2003-08-07

  The three dimensional structure of acyl-homoserine lactone synthases, and particularly Esal and Lasl, and uses thereof. Novel acyl-homoserie lactone synthases from mycobacteria, nuclei acid molecules encoding such synthases, recombinant molecules and host cells, and uses thereof.
• Long-Chain Acyl-Homoserine Lactones from <i>Methylobacterium mesophilicum:</i> Synthesis and Absolute Configuration
  作者：Armando M. Pomini、Pedro L. R. Cruz、Cláudia Gai、Welington L. Araújo、Anita J. Marsaioli

  DOI：10.1021/np900043j

  日期：2009.12.28

  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.