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Merck
CN

O9264

Sigma-Aldrich

N -(3-氧代十四烷酰)- L -高丝氨酸内酯

≥98% (TLC)

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经验公式(希尔记法):
C18H31NO4
分子量:
325.44
MDL编号:
UNSPSC代码:
12352209
eCl@ss:
32160406
PubChem化学物质编号:
NACRES:
NA.26

检测方案

≥98% (TLC)

质量水平

形式

powder

颜色

white

应用

cell analysis

运输

wet ice

储存温度

−20°C

SMILES字符串

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

InChI

1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1

InChI key

YQFJJDSGBAAUPW-INIZCTEOSA-N

应用

N-(3-氧代十四酰基)-L-高丝氨酸内酯 (3-Oxo-C14-HSL) 是酰基高丝氨酸内酯家族的一员,可能作为一种信号分子参与细菌群体感应的调节,用于确定其操作机制和特异性。

生化/生理作用

N-(3-氧代十四酰)-L-高丝氨酸内酯 (3-oxo-C14-HSL) 是一组高丝氨酸内酯中的一种,包括 N-辛酰-高丝氨酸内酯 (N-C8-HSL)、N-(3-氧代癸酰)高丝氨酸-L-内酯 (3-oxo-C10 HSL)、N-(3-氧代十二酰)高丝氨酸-L-内酯 (3-oxo-C12-HSL)、N-(3-羟基癸酰)-L-高丝氨酸内酯和 N-(3-羟基辛酰)-L-高丝氨酸内酯,参与细菌群体感应过程。这些高丝氨酸内酯被用于研究细菌群体感应的过程和机制。
酰基高丝氨酸内酯被苜蓿中华根瘤菌小肠结肠炎耶尔森菌和其他革兰氏阴性细菌用作群体信号的自身诱导剂。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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Rumana Rashid et al.
Microbes and environments, 26(2), 144-148 (2011-04-20)
N-Acylhomoserine lactones (AHLs) are used as quorum-sensing signaling molecules by many Gram-negative bacteria. Here, 413 bacterial strains were obtained from the roots of potato plants and screened for AHL-degrading bacteria using Chromobacterium violaceum reporter strains. Sixty one isolates degraded N-hexanoyl-L-homoserine
John F Teiber et al.
Methods in molecular biology (Clifton, N.J.), 692, 291-298 (2010-10-30)
Mammalian paraoxonases (PONs) are a unique, highly conserved family of calcium-dependent esterases consisting of PON1, PON2, and PON3. The PONs can hydrolyze the lactone ring of a range of N-acyl-L: -homoserine lactone (AHL) quorum sensing signaling molecules, rendering them inactive.
Bijay K Khajanchi et al.
Infection and immunity, 79(7), 2646-2657 (2011-05-04)
Aeromonas hydrophila leads to both intestinal and extraintestinal infections in animals and humans, and the underlying mechanisms leading to mortality are largely unknown. By using a septicemic mouse model of infection, we showed that animals challenged with A. hydrophila die
Mair E A Churchill et al.
Methods in molecular biology (Clifton, N.J.), 692, 159-171 (2010-10-30)
Quorum sensing plays a central role in regulating many community-derived symbiotic and pathogenic relationships of bacteria, and as such has attracted much attention in recent years. Acyl-homoserine lactones (AHLs) are important signaling molecules in the quorum sensing gene-regulatory processes found
Manabu Horikawa et al.
Bioorganic & medicinal chemistry letters, 16(8), 2130-2133 (2006-02-08)
The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition

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