N-辛酰基-DL-高丝氨酸内酯(2-8℃) | 106983-30-6

• 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-辛酰基-DL-高丝氨酸内酯(2-8℃)
• 英文名称: N-octanoylhomoserine lactone
• 英文别名: 3-octanoylamino-dihydro-furan-2-one；N-octanoyl-DL-homoserine lactone；N-(2-oxooxolan-3-yl)octanamide
• CAS: 106983-30-6
• 化学式: C₁₂H₂₁NO₃
• mdl: MFCD01862915
• 分子量: 227.304
• InChiKey: JKEJEOJPJVRHMQ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1958.9

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  N-辛酰基-DL-高丝氨酸内酯(2-8℃) 在 sodium azide 、 三氟甲磺酸酐 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以56%的产率得到3-(5-n-heptyl-1H-tetrazol-1-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007
• 作为产物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 、 辛酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以67%的产率得到N-辛酰基-DL-高丝氨酸内酯(2-8℃)
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007

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。
• 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.
• 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