N-Acyl-homoserine lactones

Figure 1 N-acyl homoserine lactone nucleotides produced by some bacterial species and their phenotype function (From Refs. 34 and 35).

S. Swift, N. J. Bainton, and M. K. Winson, Gram-negative bacterial eommunication by N-acyl homoserine lactones a universal language Trends Microbiol. 2 193 (1994). 

To-date, compounds reported to regulate population density dependent behaviours include N-acyl-homoserine lactones, among plant associated Proteobacteria (Eberl, 1999 Fuqua et al., 2001), a-butryolactone in the Streptomyces (Yamada and Nihira, 1998), oligopeptides in a variety of gram-positive species (Dunny and Winans, 1999 Kleerebezem and Quadri, 2001), cyclic dipeptides in some gram-negative species (Holden et al., 1999) and fatty acid and butyrolactone derivatives in the plant pathogenic bacteria Xanthomonas campestris and Ralstonia solanacearum (Barber et al., 1997). 

Eberl, L. N-acyl homoserine lactone mediated gene regulation in gram-negative bacteria. Syst Appl Microbiol 1999 22 493-506. 

Winson MK, Swift S, Fish L, Throup JP, Jorgensen F, Chhabra SR, Bycroft BW, Williams P, Stewart GS (1998) Construction and analysis of luxCDABE-based plasmid sensors for investigating N-acyl homoserine lactone-mediated quorum sensing. FEMS Microbiol Lett 163 185... 

Figure 1. Transcriptionally regulated network of exopolysaccharide galactoglucan biosynthesis in the Gram-negative soil bacterium S. meliloti that is affected by extracellular phosphate concentration and bacterial population density (AHL, N-acyl homoserine lactone HL, homoserine lactone).

Jafra S, Przysowa J, Czajkowski R, Michta A, Garbeva P, Van der Wolf JM. Detection and characterization of bacteria from the potato rhizosphere degrading N-acyl-homoserine lactone. Can. J. Microbiol. 2006 52 1006-1015. 

Nasser W, Bouillant ML, Salmond G, Reverchon S. Characterization of the Erwinia chrysanthemi expl-expR locus directing the synthesis of two N-acyl-homoserine lactone signal molecules. Mol. Microbiol. 1998 29 1391-1405. 

Welch M, Todd DE, Whitehead NA, McGowan SJ, Bycroft BW, Salmond GP. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J. 2000 19 631-641. 

Kaufmann GE, Sartorio R, Lee SH, Mee JM, Altobell LJ, 3rd, Ku-jawa DP, Jeffries E, Qapham B, Meijler MM, Janda KD. Antibody interference with N-acyl homoserine lactone-mediated bacterial quorum sensing. J. Am. Chem. Soc. 2006 128 2802-2803. 

Detection and Inhibition of N-Acylated Homoserine Lactone Quorum Sensing... 

This compound is also named "small bacteriocin" (Desriac etal., 2010 Lowery etal., 2010) Figure 25.3 Examples of N-acyl homoserine lactones. 

---