A-Acyl homoserine lactones

In vivo effects of single or combined A-acyl homoserine lactone quorum sensing signals on the performance of Macrobrachium rosenbergii larvae. Aquaculture, 288,233-238. 

A-acyl homoserine lactone-degrading microbial enrichment cultures isolated from Penaeus vannamei shrimp gut and their probiotic properties in Brachionus plicatilis cultures, FEMS Microbiol Ecol, 62, 45-53. 

Bacterial virulence in gram-negative bacteria is mediated by A-acyl homoserine lactones (39) in a complex pathway, and amines are candidate inhibitors (Scheme 10). However, amines are not very reactive towards y-lactones and this offered an opportunity to test whether thioureas could catalyse the process via their known role as agents capable of deploying their two NH groups to activate the C=0 group. In a model of... 

Nieto-Penalver CG, Bertini EV, de Figueroa LIC (2012) Identification of A-acyl homoserine lactones produced by Gluconacetobacter diazotrophicus PAL5 cultured in complex and synthetic media. Arch Microbiol 194 615-622... 

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. 

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)...

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... 

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). 

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. 

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. 

Figure 1 P. aeruginosa QS system. Its mechanism, (a) Biosynthesis of acyl-homoserine lactone (AHL). Abbreviations SAM, 5-adenosyl methionine ACP, acyl carrier protein, (b) General chemical structure of AHL molecules, generally called autoinducer-1 (AI-1). (c) Chemical structure of V. fischeri AI-1. (d) Chemical structure of P. aeruginosa 3-oxo-C y-HSL and (e) C4-HSL. (f) Pseuodomonas quinolone signal, PQS.

---