N-butyryl-L-Homoserine lactone-d5 (Synonyms: BHL-d5, C4-HSL-d5, PAI-2-d5)

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 spectrometryJ. Bacteriol.188(2)773-783(2006) 2.Henke, J.M., and Bassler, B.L.Bacterial social engagementsTrends in Cell Biology14(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 expressionJournal of Bacteriology184(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 aeruginosaJournal of Bacteriology183(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 synthesisJournal of Bacteriology181(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 tardaJournal of Bioscience and Bioengineering98(4)274-281(2004) 7.Luo, Z.Q., 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 consequencesJournal of Bacteriology186(19)5665-5672(2003)