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DL-Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
2-amino-4-hydroxybutanoic acid
DL-HomoSer-OH; DL-2-Amino-4-hydroxybutyric acid; (RS)-2-Amino-4-hydroxybutyric acid; DL HomoSer OH
Related CAS
6027-21-0 (D-isomer)
White crystalline powder
≥ 98% (Assay)
1.312 g/cm3
Melting Point
Store at RT.
InChI Key
Canonical SMILES
1. Quorum-sensing molecules: Sampling, identification and characterization of N-acyl-homoserine lactone in Vibrio sp
Noha Laj, Muhammed Elayadeth-Meethal, V Aldous J Huxley, Raishy R Hussain, Mohamed Saheer Kuruniyan, Punnoth Poonkuzhi Naseef Saudi J Biol Sci. 2022 Apr;29(4):2733-2737. doi: 10.1016/j.sjbs.2021.12.062. Epub 2022 Jan 4.
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.
2. N-3-Hydroxy Dodecanoyl-DL-homoserine Lactone (OH-dDHL) Triggers Apoptosis of Bone Marrow-Derived Macrophages through the ER- and Mitochondria-Mediated Pathways
Kyungho Woo, Dong Ho Kim, Man Hwan Oh, Ho Sung Park, Chul Hee Choi Int J Mol Sci. 2021 Jul 15;22(14):7565. doi: 10.3390/ijms22147565.
Quorum sensing of Acinetobacter nosocomialis for cell-to-cell communication produces N-3-hydroxy dodecanoyl-DL-homoserine lactone (OH-dDHL) by an AnoR/I two-component system. However, OH-dDHL-driven apoptotic mechanisms in hosts have not been clearly defined. Here, we investigated the induction of apoptosis signaling pathways in bone marrow-derived macrophages treated with synthetic OH-dDHL. Moreover, the quorum-sensing system for virulence regulation was evaluated in vivo using wild-type and anoI-deletion mutant strains. OH-dDHL decreased the viability of macrophage and epithelial cells in dose- and time-dependent manners. OH-dDHL induced Ca2+ efflux and caspase-12 activation by ER stress transmembrane protein (IRE1 and ATF6a p50) aggregation and induced mitochondrial dysfunction through reactive oxygen species (ROS) production, which caused cytochrome c to leak. Pretreatment with a pan-caspase inhibitor reduced caspase-3, -8, and -9, which were activated by OH-dDHL. Pro-inflammatory cytokine and paraoxonase-2 (PON2) gene expression were increased by OH-dDHL. We showed that the anoI-deletion mutant strains have less intracellular invasion compared to the wild-type strain, and their virulence, such as colonization and dissemination, was decreased in vivo. Consequently, these findings revealed that OH-dDHL, as a virulence factor, contributes to bacterial infection and survival as well as the modification of host responses in the early stages of infection.
3. Improvement in calcified anaerobic granular sludge performance by exogenous acyl-homoserine lactones
Meiling Li, Yueru Wu, Zhiwei Wang, Wencai Fu, Wenhao Dang, Yongli Chen, Yi Ning, Shuangfei Wang Ecotoxicol Environ Saf. 2021 Mar 1;210:111874. doi: 10.1016/j.ecoenv.2020.111874. Epub 2021 Jan 8.
Given the high content of Ca2+ in waste paper recycling wastewater, the anaerobic granular sludge (AnGS) undergoes calcification during wastewater treatment and affects the treatment efficiency. To restore the activity of calcified AnGS and improve the performance of AnGS, four types of N-acyl-homoserine lactones (AHLs) were added to the AnGS system while papermaking wastewater treatment. The addition of N-butyryl-DL-homoserine lactone(C4-HSL) and N-octanoyl-DL-homoserine lactone (C8-HSL) had an inhibitory affect the COD removal efficiency and SMA of sludge at the inception. The addition of N-hexanoyl-L-homoserine lactone (C6-HSL) has no obvious effect on the COD removal efficiency, but can improve the SMA of sludge more obviously. The addition of N-(β-ketocaproyl)-DL-homoserine lactone (3O-C6-HSL) can increased COD removal efficiency and promoted SMA together obviously. The addition of C6-HSL and 3O-C6-HSL can increase volatile suspended solid (VSS)/total suspended solid (TSS), and regulate extracellular polymeric substance (EPS) secretion in AnGS. Analysis of microbial sequencing revealed changes in the microbial community structure following AHL addition, which enhanced the methane metabolism pathway in sludge. The addition of C6-HSL, C8-HSL, and 3O-C6-HSL increased Methanosaeta population, thus increasing the aceticlastic pathway in sludge. Thus, exogenous AHLs can play an important role in regulating microbial community structure, and in improving the performance of AnGS.
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