143537-62-6
Chemical Structure
N-(3-Oxohexanoyl)-L-homoserine lactone
Synonym(s): OHHL;N-(3-Oxohexanoyl)homoserine lactone
- CAS No.: 143537-62-6
- Formula:C10H15NO4
- Molecular Weight:213.23
IUPAC Name: (S)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)hexanamide
InChIKey: YRYOXRMDHALAFL-QMMMGPOBSA-N
SMILES: CCCC(CC(N[C@@H]1C(OCC1)=O)=O)=O
Biological Activity: N-(3-Oxohexanoyl)-L-homoserine lactone (OHHL; N-(3-Oxohexanoyl)homoserine lactone) is a specific agonist of LuxR-type transcription factor CarR with a Kd of 1.8 μM. N-(3-Oxohexanoyl)-L-homoserine lactone activates CarR by inducing protein multimerization, promoting its binding to target DNA sequences in the carR-carA intergenic region, thereby upregulating the transcription of carbapenem biosynthesis genes. N-(3-Oxohexanoyl)-L-homoserine lactone acts as a quorum sensing signal molecule, enabling bacteria to coordinate the production of carbapenem antibiotics in a cell density-dependent manner. N-(3-Oxohexanoyl)-L-homoserine lactone is used to study bacterial quorum sensing mechanisms, especially the secondary metabolism and virulence factor regulatory pathways of Erwinia carotovora and Yersinia enterocolitica[1][2][3].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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N-(3-Oxohexanoyl)-L-homoserine lactone | 99.76% | N-(3-Oxohexanoyl)-L-homoserine lactone (OHHL; N-(3-Oxohexanoyl)homoserine lactone) is a specific agonist of LuxR-type transcription factor CarR with a Kd of 1.8 μM. N-(3-Oxohexanoyl)-L-homoserine lactone activates CarR by inducing protein multimerization, promoting its binding to target DNA sequences in the carR-carA intergenic region, thereby upregulating the transcription of carbapenem biosynthesis genes. N-(3-Oxohexanoyl)-L-homoserine lactone acts as a quorum sensing signal molecule, enabling bacteria to coordinate the production of carbapenem antibiotics in a cell density-dependent manner. N-(3-Oxohexanoyl)-L-homoserine lactone is used to study bacterial quorum sensing mechanisms, especially the secondary metabolism and virulence factor regulatory pathways of Erwinia carotovora and Yersinia enterocolitica. | ||||||||||||||||||||
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- [1]. Welch M, et al. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J. 2000 Feb 15;19(4):631-41. [Content Brief]
- [2]. Bainton NJ, et al. N-(3-oxohexanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem J. 1992 Dec 15;288 ( Pt 3)(Pt 3):997-1004. [Content Brief]
- [3]. Jacobi CA, et al. Detection of N-(3-oxohexanoyl)-L-homoserine lactone in mice infected with Yersinia enterocolitica serotype O8. Infect Immun. 2003 Nov;71(11):6624-6. [Content Brief]
