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N-butyryl-L-Homocysteine thiolactone Exclusive

Cayman Chemical Item Number 10011204

(CAS 202284-85-3)

N-butyryl-L-Homocysteine thiolactone (CAS 202284-85-3)

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Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-butyryl-L-Homocysteine thio-lactone is an analog of N-butyryl-L-homoserine lactone, the small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and cellular metabolism.1 N-butyryl-L-Homocysteine thio-lactone induces violacein expression in C. violaceum mutants usually not able to produce AHLs.1,2

1 Ikeda, T., Kajiyama, K., Kita, T., et al. The synthesis of optically pure enantiomers of N-acyl-homoserine lactone autoinducers and their analogues. Chem Lett 314-315 (2001).

2 McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 143 3703-3711 (1997).

Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​thienyl]-​butanamide
CAS Number 202284-85-3
Molecular Formula C8H13NO2S
Formula Weight 187.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCC(=O)​N[C@H]​1CCSC1=O

Background Reading

Ikeda, T., Kajiyama, K., Kita, T., et al. The synthesis of optically pure enantiomers of N-acyl-homoserine lactone autoinducers and their analogues. Chem Lett 314-315 (2001).

McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 143 3703-3711 (1997).
Size Price Quantity Subtotal
5 mg $26.00 $0.00
10 mg $49.00 $0.00
25 mg $117.00 $0.00
50 mg $208.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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