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Merck
CN

44558

Sigma-Aldrich

N -辛酰- L -高丝氨酸内酯

≥96% (HPLC)

别名:

N - [(3 S )-四氢-2-氧代-3-呋喃基] 辛酰胺, C8-HSL

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About This Item

经验公式(希尔记法):
C12H21NO3
分子量:
227.30
Beilstein:
8148282
MDL编号:
UNSPSC代码:
12352211
PubChem化学物质编号:
NACRES:
NA.85

产品名称

N -辛酰- L -高丝氨酸内酯, ≥96% (HPLC)

质量水平

方案

≥96% (HPLC)

表单

powder or crystals

旋光性

[α]/D -28±3°, c = 0.2 in methanol

颜色

white to off-white

适用性

conforms to structure for Proton NMR spectrum

应用

detection

储存温度

−20°C

SMILES字符串

O=C1OCC[C@@H]1NC(CCCCCCC)=O

InChI

1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1

InChI key

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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生化/生理作用

N -辛酰- L -高丝氨酸内酯是 N -酰基高丝氨酸内酯家族的成员。 N -酰基高丝氨酸内酯 (AHL) 调控革兰阴性菌如 埃希杆菌沙门菌的基因表达,参与群体感应、定植、化学防御 和细菌间的细胞间通讯;综述见 AHL 在革兰氏阳性菌中作为寡肽释放,在革兰氏阴性菌中作为群体信号释放。细菌细胞间通讯已成为开发新型抗毒力药物的靶点,,也是预防生物膜形成的研究热点。
群体感应信号产生

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
A Kuo et al.
Journal of bacteriology, 178(4), 971-976 (1996-02-01)
Population density-dependent expression of luminescence in Vibrio fischeri is controlled by the autoinducer N-3-oxohexanoyl-L-homoserine lactone (autoinducer 1 [AI-1]), which via LuxR activates transcription of the lux operon (luxICDABEG, encoding the putative autoinducer synthase [LuxI] and the luminescence enzymes). We recently
José Gomes et al.
Chemical communications (Cambridge, England), 49(2), 155-157 (2012-11-22)
We demonstrate the synthesis and immobilization of natural product hybrids featuring an acyl-homoserine lactone and a nitrodopamine onto biocompatible TiO(2) surfaces through an operationally simple dip-and-rinse procedure. The resulting immobilized hybrids were shown to be powerful quorum sensing (QS) activators
Mattia Marenda et al.
Scientific reports, 6, 39142-39142 (2016-12-15)
Bacterial communities undergo collective behavioural switches upon producing and sensing diffusible signal molecules; a mechanism referred to as Quorum Sensing (QS). Exemplarily, biofilm organic matrices are built concertedly by bacteria in several environments. QS scope in bacterial ecology has been
J B Andersen et al.
Applied and environmental microbiology, 67(2), 575-585 (2001-02-07)
In order to perform single-cell analysis and online studies of N-acyl homoserine lactone (AHL)-mediated communication among bacteria, components of the Vibrio fischeri quorum sensor encoded by luxR-P(luxI) have been fused to modified versions of gfpmut3* genes encoding unstable green fluorescent

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