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N- (3-Oxohexanoyl) -L-homoserine lactone

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].

Product Specifications

CAS Number

143537-62-6

Product Name Alternative

OHHL; N- (3-Oxohexanoyl) homoserine lactone

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Bacterial

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/n-3-oxohexanoyl-l-homoserine-lactone.html

Purity

99.93

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

CCCC(CC(N[C@@H]1C(OCC1)=O)=O)=O

Molecular Formula

C10H15NO4

Molecular Weight

213.23

Precautions

H302, H315, H319, H335

References & Citations

[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.|[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.|[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.

Shipping Conditions

Blue Ice

Storage Conditions

-20°C, 3 years (Powder)

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Available Sizes

Frequently Asked Questions

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