Structural identification of autoinducer of Photobacterium fischeri luciferase

Citations Over TimeTop 22% of 1981 papers

Abstract

Synthesis of bacterial luciferase in some strains of luminous bacteria requires a threshold concentration of an autoinducer synthesized by the bacteria and excreted into the medium. Autoinducer excreted by Photobacterium fischeri strain MJ-1 was isolated from the cell-free medium by extraction with ethyl acetate, evaporation of solvent, workup with ethanol-water mixtures, and silica gel chromatography, followed by normal-phase and then reverse-phase high-performance liquid chromatography. The final product was greater than 99% pure. The structure of the autoinducer as determined by high-resolution 1H nuclear magnetic resonance spectroscopy, infrared spectroscopy, and high-resolution mass spectrometry was N-(3-oxohexanoly)-3-aminodihydro-2(3H)-furanone [or N-(beta-ketocaproyl)homoserine lactone]. The formation of homoserine by hydrolysis of the autoinducer was consistent with this structure. Synthetic autoinducer, obtained as a racemate, was prepared by coupling homoserine lactone to the ethylene glycol ketal of sodium 3-oxohexanoate, followed by mildly acidic removal of the protecting group; this synthetic material showed the appropriate biological activity.

Related Papers

• → Inhibition of Quorum Sensing in Pseudomonas aeruginosa by N -Acyl Cyclopentylamides(2007)186 cited
• → New insights into the regulatory mechanisms of the LuxR family of quorum sensing regulators(2006)115 cited
• → Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers(2002)89 cited
• → Quorum sensing autoinducers: Do they play a role in natural microbial habitats?(1998)35 cited
• → Detection of quorum-sensing-related molecules in Vibrio scophthalmi(2008)24 cited