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Merck
CN

O1764

Sigma-Aldrich

N-(3-氧代辛酰基)-L-高丝氨酸内酯

≥97% (HPLC), white, powder

别名:

3-oxo-C8-HSL, 3OC8-HSL, N-(β-酮辛酰基)-L-高丝氨酸

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关于此项目

经验公式(希尔记法):
C12H19NO4
化学文摘社编号:
分子量:
241.28
MDL编号:
UNSPSC代码:
12352202
eCl@ss:
32160406
PubChem化学物质编号:
NACRES:
NA.32
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方案

≥97% (HPLC)

表单

powder

分子量

241.28

技术

protein expression: suitable

颜色

white

溶解性

chloroform: 50 mg/mL, clear, colorless

运输

wet ice

储存温度

−20°C

SMILES字符串

CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O

InChI

1S/C12H19NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h10H,2-8H2,1H3,(H,13,15)/t10-/m0/s1

InChI key

FXCMGCFNLNFLSH-JTQLQIEISA-N

一般描述

N-(3-氧代辛酰基)-L-高丝氨酸内酯是一种常见的群体感应(QS)信号。
它是一种由革兰氏阴性菌产生的信号分子。

应用

N-(3-氧代辛酰基)-L-高丝氨酸内酯已用于:
  • 研究pH、温度和盐度对假单胞菌生物膜的胞外聚合物物质(EPS)的影响。
  • 作为AHL诱导剂激活长聚球藻群体感知途径。

生化/生理作用

N-(3-氧代辛酰基)-L-高丝氨酸内酯可刺激tra基因的表达。它是一种自诱导剂和强效拮抗剂。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Developing Cyanobacterial Quorum Sensing Toolkits: Toward Interspecies Coordination in Mixed Autotroph/Heterotroph Communities
Kokarakis EJ, et al.
ACS Synthetic Biology, 12(1), 265-276 (2023)
J Zhu et al.
Journal of bacteriology, 180(20), 5398-5405 (1998-10-10)
The TraR and TraI proteins of Agrobacterium tumefaciens mediate cell-density-dependent expression of the Ti plasmid tra regulon. TraI synthesizes the autoinducer pheromone N-(3-oxooctanoyl)-L-homoserine lactone (3-oxo-C8-HSL), while TraR is an 3-oxo-C8-HSL-responsive transcriptional activator. We have compared the abilities of 3-oxo-C8-HSL and
S Swift et al.
Molecular microbiology, 10(3), 511-520 (1993-11-01)
The pheromone N-(3-oxohexanoyl)-L-homoserine lactone (OHHL) regulates expression of bioluminescence in the marine bacterium Vibrio fischeri, the production of carbapenem antibiotic in Erwinia carotovora and exoenzymes in both E. carotovora and Pseudomonas aeruginosa. A characteristic feature of this regulatory mechanism in
J Zhu et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(9), 4832-4837 (1999-04-29)
TraR is an Agrobacterium transcriptional regulator whose activity requires the pheromone N-3-oxooctanoyl-L-homoserine lactone. TraR was purified as a complex with the pheromone and contained one pheromone molecule per protein monomer. TraR-pheromone complexes bound to a single DNA site and activated
Siqing Xia et al.
Journal of environmental sciences (China), 24(12), 2035-2040 (2012-01-01)
N-acyl-homoserines quenching, enzymatic quenching of bacterial quorum sensing, has recently applied to mitigate biofilm in membrane bioreactor. However, the effect of AHLs on the behavior of biofilm formation is still sparse. In this study, Pseudomonas aeruginosa biofilm was formed on

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