N-butyryl-L-Homoserine lactone-d5

N-butyryl-L-Homoserine lactone-d₅ is intended for use as an internal standard for the quantification of N-butyryl-L-homoserine lactone by GC- or LC-MS. N-butyryl-L-Homoserine lactone is a quorum-sensing signaling molecule produced by P. aeruginosa.¹ It induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 μM.² N-butyryl-L-Homoserine lactone (50 μM) induces rhamnolipid accumulation in P. aeruginosa growth media.³

N-butyryl-L-Homoserine lactone-d5 is the deuterium labeled N-Butanoyl-L-homoserine lactone. N-Butanoyl-L-homoserine lactone (C4-HSL) is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). N-Butanoyl-L-homoserine lactone has antibacterial activity and is used in antibacterial biofilm[1]. N-Butanoyl-L-homoserine lactone aptamers blocks qurom sensing and inhibits biofilm formation in Pseudomonas aeruginosa[2][3].

1. Pearson, J.P., Passador, L., Igleweski, B.H., et al. A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa Proc. Natl. Acad. Sci. USA 92(5),1490-1494(1995).
2. 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. 30(4),314-315(2001).
3. Schooling, S.R., Charaf, U.K., Allison, D.G., et al. A role for rhamnolipid in biofilm dispersion Biofilm 1(2),91-99(2004).