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

CHF 68.00
In stock
CDX-O0057-M01010 mgCHF 68.00
CDX-O0057-M05050 mgCHF 244.00
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Product Details
Synonyms 3-oxo-C6-HSL; N-(β-Ketocaproyl)-L-homoserine lactone
Product Type Chemical
Formula C10H15NO4
MW 213.2
CAS 143537-62-6
Source/Host Chemicals Synthetic.
Purity Chemicals ≥97% (GC)
Appearance White solid.
Solubility Soluble in chloroform (>100mg/ml).
Identity Determined by NMR.
Declaration Manufactured by Chemodex.
Other Product Data

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Smiles [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCC
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Specification Sheet
Datasheet Download PDF

N-(3-Oxohexanoyl)-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. At increased populations of bacteria, localized higher concentrations of 3OC6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ 3OC6-HSL in cell-to-cell communication. An autoinducer of P. fischeri luciferase and a specfic genetic regulator that is unrelated to at least one of the enzyme systems that it induces. It acts after excretion and accumulation in the extracellular medium.

Product References

(1) A. Eberhard, et al.; Arch. Microbiol. 146, 35 (1986) | (2) N.J. Bainton, et al.; Biochem. J. 288, 997 (1992) | (3) P. Williams, et al.; FEMS Microbiol. Lett. 100, 161 (1992) | (4) R.H. Gomer; Curr. Biol. 4, 734 (1994) | (5) A. Chatterjee, et al.; Appl. Environ.Microbiol. 61, 1959 (1995) | (6) Y.H. Dong, et al.; Nature 411, 813 (2001) | (7) G.D. Geske, et al.; Bioorg. Med. Chem. Lett. 18, 5978 (2008) | (8) R.L. Frey, et al.; Environ. Sci. Tech. 44, 7465 (2010)

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