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3-氧代-N-[(3S)-2-氧代四氢呋喃-3-基]辛酰胺

用途

N-3-氧代-辛酰基-L-高丝氨酸内酯是一种群体感应信号,是一种农杆菌自诱导剂[1][2]。

名称

[ CAS 号 ]:
147795-39-9

[ 中文名 ]:
3-氧代-N-[(3S)-四氢-2-氧代-3-呋喃基]辛酰胺

[ 英文名 ]:
N-3-Oxo-octanoyl-L-homoserine lactone

[中文别名 ]:

[英文别名 ]:

Aai-OOHL
LAE
HSL-OOA
OOHL
N-(3-Oxooctanoyl)-L-homoserine lactone
3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]octanamide

生物活性

[ 描述 ]:

N-3-氧代-辛酰基-L-高丝氨酸内酯是一种群体感应信号,是一种农杆菌自诱导剂[1][2]。

[ 相关类别 ]:

研究领域 >> 感染

信号通路 >> 其他 >> 其他

[体外研究]

N-3-氧代-辛酰基-L-高丝氨酸内酯(3OC8-HSL)预处理(10 μM；两个 d)对叶片中的病原菌增殖具有强烈的抑制作用[1]。用N-3-氧代-辛酰基-L-高丝氨酸内酯处理的植物显示出防御相关酶的活性增加,包括过氧化物酶、过氧化氢酶、苯丙氨酸解氨酶和超氧化物歧化酶[1]。

[参考文献]

[1]. Fang Liu, et al. N-3-oxo-octanoyl-homoserine lactone-mediated priming of resistance to Pseudomonas syringae requires the salicylic acid signaling pathway in Arabidopsis thaliana. BMC Plant Biol. 2020 Jan 28;20(1):38.

[2]. Hai-Bao Zhang, et al. Genetic control of quorum-sensing signal turnover in Agrobacterium tumefaciens. Proc Natl Acad Sci U S A

物理化学性质

[ 密度 ]:
1.12g/cm3

[ 沸点 ]:
490.1ºC at 760mmHg

[ 熔点 ]:
96-97 ºC (ethyl acetate )

[ 分子式 ]:
C₁₂H₁₉NO₄

[ 分子量 ]:
241.28

[ 闪点 ]:
250.2ºC

[ 精确质量 ]:
241.131409

[ PSA ]:
72.47000

[ LogP ]:
1.73860

[ 外观性状 ]:
White solid Chemodex

[ 蒸汽压 ]:
9.41E-10mmHg at 25°C

[ 折射率 ]:
1.484

[ 储存条件 ]:
-20°C

[ 水溶解性 ]:
Slightly soluble (7.2 g/L) (25 ºC)

MSDS

详细MSDS(安全技术说明书)

安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危险品运输编码 ]:
NONH for all modes of transport

文献

Medicinal chemistry as a conduit for the modulation of quorum sensing.

J. Med. Chem. 53 , 7467-89, (2010)

Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators.

Bioorg. Med. Chem. Lett. 18 , 5978-81, (2008)

A focused library of N-aryl l-homoserine lactones was designed around known lactone leads and evaluated for antagonistic and agonistic activity against quorum-sensing receptors in Agrobacterium tumefa...

Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.

Bioorg. Med. Chem. Lett. 18 , 3072-5, (2008)

The transcription factor QscR is a regulator of quorum sensing in Pseudomonas aeruginosa and plays a role in controlling virulence in this prevalent opportunistic pathogen. This study outlines the dis...

更多文献