Acylated homoserine lactone

Bruns A, H Cypionka, J Overmann (2002) Cyclic AMP and acyl homoserine lactones increase cultivation efficiency of heterotrophic bacteria from the Central Baltic Sea. Appl Environ Microbiol 68 3978-3987. 

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). 

Fig. 11.1 Characteristic acyl homoserine lactones (AHLs) (a-c) are structurally similar to representative halogenated furanones (d-f) reported from Delisea pulchra (de Nys et al. 1993 Gould et al. 2006)...

Borchardt SA, Allain EJ, Michels JJ, Stearns GW, Kelly RF, McCoy WF (2001) Reaction of acylated homoserine lactone bacterial signaling molecules with oxidized halogen antimicrobials. Appl Environ Microbiol 67 3174-3179... 

Wheeler GL, Tait K, Taylor A, Brownlee C, Joint I (2006) Acyl-homoserine lactones modulate the settlement rate of zoospores of the marine alga Ulva intestinalis via a novel chemokinetic mechanism. Plant Cell Environ 29 608-618... 

Funqua, C., Parsek, M. R., and Greenberg, E. P. (2001). Regulation of gene expression by cell-to-cell communication acyl-homoserine lactone quorum sensing. Ann. Rev., Genet., 35, 439-68. 

Shiner, E. K., Rumbaugh, K. R, and Williams, S. C. (2005). Interkingdom signaling deciphering the language of acyl homoserine lactones. FEMS Microbiol Rev, 29, 935 7. 

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). 

Dong, Y.H, Xu, J.L., Li, X.Z., Zhang, L.H. AiiA, an enzyme that inactivates the acyl-homoserine lactone quomm sensing signal and attenuates the virulence of Erwinia carotovora. Proc Natl Sci 2000 97 3526-3531. 

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

Leadbetter, J.R., Greenberg, E.P. Metabolism of acyl-homoserine lactone quomm-sensing signals by Variovorax paradoxus. J Bacterid 2000 182 6921-6926. 

Lin, Y.H., Xu, J.L., Hu, J., Wang, L.H., Ong, S.L., Leadbetter, J.R., Zhang, L.H. Acyl- homoserine lactone acylase from Ralstonia strain XJ12B represents a novel and potent class of quorum-quenching enzymes. Mol Microbiol 2003 47 849-860. 

Parsek, M.R., Val, D.L., Hanzelka, B.L., Cronan, J.E. Jr., Greenberg E.P. Acyl homoserine-lactone quorumsensing signal generation. Proc Natl Acad Sci USA. 1999 13 4360-4365. 

Small organic molecules such as acylated homoserine lactones have been implicated in gene expression in marine bacteria and in signaling or sensing processes between bacterial communities.28 Structurally related secondary metabolites, e.g., Structures 2.7 and 2.8, have been detected in marine bacterial isolates,2930 where they may be involved in signaling or alternately interfere with this process in competing bacterial strains. 

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).

Altering substrate specificity sometimes follows a process of relaxing, followed by tightening. Collins et al. (47) used a clever dual selection strategy to alter the response of the LuxR transcription factor to different acyl-homoserine lactones. This type of research can produce modifiers of transcription with fine control by a desired ligand chosen so as to not interfere with other biological pathways. The response of LuxR was initially broadened from 3-oxo-hexanoyl-homoserine lactone (30C6HSL)... 

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. 

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