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N-butyryl-L-Homoserine lactone-d5

Cayman Chemical Item Number 10007899

C4-HSL-d5

N-butyryl-L-Homoserine lactone-d5

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Description

N-butyryl-L-Homoserine lactone-d5 (C4-HSL-d5) contains five deuterium atoms at the 3, 3', 4, 4, and 4 positions. It is intended for use as an internal standard for the quantification of C4-HSL by GC- or LC-mass spectrometry. Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. 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. C4-HSL is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism.1 The diverse applications of this molecule include regulation of virulence in general, infection prevention, and formation of biofilms.2,3,4,5,6,7

1 Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J Bacteriol 188(2) 773-783 (2006).

2 Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

3 Diggle, S.P., Winzer, K., Lazdunski, A., et al. Advancing the quorum in pseudomonas aeruginosa: MvaT and the regulation of n-acylhomoserine lactone production and virulence gene expression. J Bacteriol 184(10) 2576-2586 (2002).

4 Pessi, G., Williams, F., Hindle, Z., et al. The global posttranscriptional regulator RsmA modulates production of virulence determinants and N-acylhomoserine lactones in pseudomonas aeruginosa. J Bacteriol 183(22) 6676-6683 (2001).

5 Hoang, T.T., and Schweizer, H.P. Characterization of pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): A target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis. J Bacteriol 181(17) 5489-5497 (1999).

6 Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen edwardsiella tarda. J Biosci Bioeng 98(4) 274-281 (2004).

7 Luo, Z., Su, S., and Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J Bacteriol 186(19) 5665-5672 (2003).

Synonyms
  • C4-HSL-d5
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​butanamide-​3,​3,​4,​4,​4-​d5
Molecular Formula C8H8D5NO3
Formula Weight 176.2
Formulation A crystalline solid
Purity ≥99% deuterated forms (d1-d5)
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCC(=O)​N[C@H]​1CCOC1=O

Background Reading

Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J Bacteriol 188(2) 773-783 (2006).

Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

Luo, Z., Su, S., and Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J Bacteriol 186(19) 5665-5672 (2003).

Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen edwardsiella tarda. J Biosci Bioeng 98(4) 274-281 (2004).

Hoang, T.T., and Schweizer, H.P. Characterization of pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): A target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis. J Bacteriol 181(17) 5489-5497 (1999).

Pessi, G., Williams, F., Hindle, Z., et al. The global posttranscriptional regulator RsmA modulates production of virulence determinants and N-acylhomoserine lactones in pseudomonas aeruginosa. J Bacteriol 183(22) 6676-6683 (2001).

Diggle, S.P., Winzer, K., Lazdunski, A., et al. Advancing the quorum in pseudomonas aeruginosa: MvaT and the regulation of n-acylhomoserine lactone production and virulence gene expression. J Bacteriol 184(10) 2576-2586 (2002).

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Size Price Quantity Subtotal
500 µg $22.00 $0.00
1 mg $42.00 $0.00
5 mg $176.00 $0.00
10 mg $308.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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