N-Acyl homoserine lactone

General chemical structure of an N-acyl homoserine lactone

N-Acyl homoserine lactones (Abbreviated as AHLs or N-AHLs) are a class of signaling molecules involved in bacterial quorum sensing. Quorum sensing is a method of communication between bacteria that enables the coordination of group-based behavior based on population density. They signal changes in gene expression, such as switching between the flagella gene and the gene for pili for the development of a biofilm.

Formation

Bacterial signalling

In bacterial signalling, N-AHLs are produced within the bacterial cell and released into the environment. N-AHLs produced by different bacteria differ in the length of the R-group side-chain. Chain lengths vary from 4 to 18 carbon atoms and in the substitution of a carbonyl at the third carbon.^[1]

Edman degradation

Homoserine lactone is also a product of the proteolytic reaction of cyanogen bromide (CNBR) with a methionine residue in a protein. This reaction is important for chemical sequencing of proteins, as the Edman degradation process is unable to sequence more than 70 consecutive residues.

In biology

General principles

The production Signaling molecules are produced within the cell and are released into the environment. The resulting concentration of signaling molecules in the environment is dependent upon population density. Once the population density has reached a particular threshold, gene expression can begin. This allows bacteria to coordinate group-based behavior. It has also been suggested that N-AHLs alter local surface tension enough to create Marangoni flows which facilitate swarming and colony motility. ^[2]

Vibrio fischeri

One example of the involvement of AHLs in quorum sensing is in the regulation of the bioluminescent protein luciferase in the luminescent bacterium Vibrio fischeri. Similar pathways occur in other luminescent bacteria. In Vibrio fischeri, AHL binds to the protein product of the LuxR gene and activates it. The C-terminal domain of activated LuxR relieves the repression exerted by H-NS nucleoid proteins that bind to the promoters of LuxR, LuxI and the LuxCDABEG operon, as well as to A-T-rich stretches within that operon and other genomic regions. The product of LuxI catalyses the synthesis of AHL. Thus, AHL acts as an autoinducer. Transcription of the LuxCDABEG operon results in luminescence due to the expression of LuxA and LuxB, which form a protein known as a luciferase and the expression of LuxC, D, E, and G, which are involved in the synthesis of the luciferase's substrate, tetradecanal. This is an important feature of quorum sensing, as it makes little sense for one cell to waste the energy producing light, as the resulting light will be so faint that it will be more or less undetectable. Instead, once the bacterial population has reached a specific size, only then does light production commence.

History

Homoserine lactones were first discovered at Cornell University.^[3]

See also

• Lactonase

Notes

1. Kumari, A.; Pasini, P.; Deo, S. K.; Flomenhoft, D.; Shashidhar, S.; Daunert, S. (2006). "Biosensing Systems for the Detection of Bacterial Quorum Signaling Molecules". Analytical Chemistry. 78 (22): 7603–7609. doi:10.1021/ac061421n. PMID 17105149.
2. Daniels, R.; Reynaert, S.; Hoekstra, H.; Verreth, C.; Janssens, J.; Braeken, K.; Fauvart, M.; Beullens, S.; Heusdens, C.; Lambrichts, I.; De Vos, D.E.; Vanderleyden, J.; Vermant J.; Michiels, J. (2006). "Quorum signal molecules as biosurfactants affecting swarming in Rhizobium etli" (PDF). PNAS. 103 (40): 14965–14970. Bibcode:2006PNAS..10314965D. doi:10.1073/pnas.0511037103. PMC 1595459. PMID 16990436.
3. Eberhard, A.; Burlingame, A. L.; Eberhard, C.; Kenyon, G. L.; Nealson, K. H.; Oppenheimer, N. J. (1981). "Structural identification of autoinducer of Photobacterium fischeri luciferase". Biochemistry. 20 (9): 2444–2449. doi:10.1021/bi00512a013. PMID 7236614.