N-(3-Oxooctanoyl)-DL-homoserine lactone
(Synonyms: N-(3-氧代辛酰基)-DL-高丝氨酸内酯(-20°C),(Rac)-3-oxo-C8-HSL) 目录号 : GC64532
N-(3-Oxooctanoyl)-DL-homoserine lacton 是由革兰氏阴性菌产生的一种 N-酰基高丝氨酸内酯 (AHL)，具有立体化学结构依赖性的植物根生长调节活性。
Cas No.:106983-27-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-(3-Oxooctanoyl)-DL-homoserine lacton is a member of N-Acyl homoserine lactone (AHL) from gram-negative bacteria, with stereochemistry-dependent growth regulatory activity for roots [1].
The S enantiomer of N-(3-Oxooctanoyl)-DL-homoserine lacton increases sprouting of roots more effectively than the R enantiomer in sugar cane[1].Both the R and S enantiomers let to stretch root cells[1].
[1]. Olher VG, et al. Acyl-homoserine Lactone from Saccharum × officinarum with Stereochemistry-Dependent Growth Regulatory Activity. J Nat Prod. 2016 May 27;79(5):1316-21.
| Cas No. | 106983-27-1 | SDF | Download SDF |
| 别名 | N-(3-氧代辛酰基)-DL-高丝氨酸内酯(-20°C),(Rac)-3-oxo-C8-HSL | ||
| 分子式 | C12H19NO4 | 分子量 | 241.28 |
| 溶解度 | DMSO : 100 mg/mL (414.46 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1446 mL | 20.7228 mL | 41.4456 mL |
| 5 mM | 0.8289 mL | 4.1446 mL | 8.2891 mL |
| 10 mM | 0.4145 mL | 2.0723 mL | 4.1446 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quorum-sensing molecules: Sampling, identification and characterization of N-acyl-homoserine lactone in Vibrio sp
Saudi J Biol Sci 2022 Apr;29(4):2733-2737.PMID:35531216DOI:10.1016/j.sjbs.2021.12.062.
Quorum sensing (QS) is a mechanism by which gram-negative bacteria regulate their gene expression by making use of cell density. QS is triggered by a small molecule known as an autoinducer. Typically, gram-negative bacteria such as Vibrio produce signaling molecules called acyl homoserine lactones (AHLs). However, their levels are very low, making them difficult to detect. We used thin layer chromatography (TLC) to examine AHLs in different Vibrio species, such as Vibrio alginolyticus, Vibrio parahemolyticus, and Vibrio cholerae, against a standard- Chromobacterium violaceum. Further, AHLs were characterised by high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). C4-HSL (N- butanoyl- L- homoserine lactone), C6-HSL (N- hexanoyl- L- homoserine lactone), 3-oxo-C8-HSL (N-(3-Oxooctanoyl)-DL-homoserine lactone), C8-HSL (N- octanoyl- L- homoserine lactone), C110-HSL (N- decanoyl- L- homoserine lactone), C12-HSL (N- dodecanoyl- L- homoserine lactone) and C14-HSL (N- tetradecanoyl- L- homoserine lactone) were identified from Vibrio. These results may provide a basis for blocking the AHL molecules of Vibrio, thereby reducing their pathogenicity and eliminating the need for antimicrobials.
Quorum Sensing Disruption in Vibrio harveyi Bacteria by Clay Materials
J Agric Food Chem 2018 Jan 10;66(1):40-44.PMID:29231719DOI:10.1021/acs.jafc.7b03918.
This work describes the use of clay minerals as catalysts for the degradation of quorum sensing molecule N-(3-Oxooctanoyl)-DL-homoserine lactone. Certain clay minerals as a result of their surface properties and porosity can catalytically degrade the quorum sensing molecule into smaller fragments. The disruption of quorum sensing by clay in a growing Gram-negative Vibrio harveyi bacteria culture was also studied by monitoring luminescence and population density of the bacteria, wherein quenching of bacterial quorum sensing activity was observed by means of luminescence reduction. The results of this study show that food-grade clays can be used as biocatalysts in disrupting bacterial activity in various media.
AHL signals induce rubrifacine production in a bruI mutant of Brenneria rubrifaciens
Phytopathology 2012 Feb;102(2):195-203.PMID:22236075DOI:10.1094/PHYTO-04-11-0111.
Several members of the bacterial genus Brenneria are pathogenic on different tree species. Cell-free extracts from the bacterial phytopathogens Brenneria rubrifaciens, B. salicis, and B. nigrifluens induced production of the red pigment rubrifacine in the B. rubrifaciens bruI insertional mutant Br-212. Analysis of the bruI locus identified an adjacent open reading frame, designated bruR, with homology to luxR. High-performance liquid chromatography and mass spectrometry analysis of ethyl acetate extracts from wild-type B. rubrifaciens and Escherichia coli expressing the bruI gene identified two acyl homoserine lactone (AHL) peaks, N-(3-oxohexanoyl)-homoserine lactone (3OC6HSL) and N-hexanoyl-homoserine lactone (C6HSL). Addition of synthetic 3OC6HSL and C6HSL at 10 μM to the bruI mutant, strain Br-212, induced rubrifacine production and the ability to elicit a hypersensitive reaction (HR) in tobacco leaves. Synthetic C6HSL was less effective at inducing pigment production than 3OC6HSL at 10 μM. The bruI mutant Br-212 did not produce detectable AHLs, indicating that C6HSL and 3OC6HSL are the major AHLs produced by this species. The AHLs N-heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-DL-homoserine lactone (C8HSL), and N-(3-Oxooctanoyl)-DL-homoserine lactone (3OC8HSL) also induced pigment production in Br-212 and restored its ability to elicit an HR in tobacco, suggesting that cross-talk with other bacterial species may be possible.