Structural identification of autoinducer of Photobacterium fischeri luciferase - PubMed (original) (raw)
Structural identification of autoinducer of Photobacterium fischeri luciferase
A Eberhard et al. Biochemistry. 1981.
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.
Similar articles
- Analogs of the autoinducer of bioluminescence in Vibrio fischeri.
Eberhard A, Widrig CA, McBath P, Schineller JB. Eberhard A, et al. Arch Microbiol. 1986 Oct;146(1):35-40. doi: 10.1007/BF00690155. Arch Microbiol. 1986. PMID: 3813773 - Multiple N-acyl-L-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri.
Kuo A, Blough NV, Dunlap PV. Kuo A, et al. J Bacteriol. 1994 Dec;176(24):7558-65. doi: 10.1128/jb.176.24.7558-7565.1994. J Bacteriol. 1994. PMID: 8002580 Free PMC article. - Autoinduction of bacterial luciferase. Occurrence, mechanism and significance.
Nealson KH. Nealson KH. Arch Microbiol. 1977 Feb 4;112(1):73-9. doi: 10.1007/BF00446657. Arch Microbiol. 1977. PMID: 843170 - Purification and structural identification of an autoinducer for the luminescence system of Vibrio harveyi.
Cao JG, Meighen EA. Cao JG, et al. J Biol Chem. 1989 Dec 25;264(36):21670-6. J Biol Chem. 1989. PMID: 2600086 - Detection and quantification of Vibrio fischeri autoinducer from symbiotic squid light organs.
Boettcher KJ, Ruby EG. Boettcher KJ, et al. J Bacteriol. 1995 Feb;177(4):1053-8. doi: 10.1128/jb.177.4.1053-1058.1995. J Bacteriol. 1995. PMID: 7860584 Free PMC article.
Cited by
- Chemical signaling in biofilm-mediated biofouling.
Liu X, Zou L, Li B, Di Martino P, Rittschof D, Yang JL, Maki J, Liu W, Gu JD. Liu X, et al. Nat Chem Biol. 2024 Sep 30. doi: 10.1038/s41589-024-01740-z. Online ahead of print. Nat Chem Biol. 2024. PMID: 39349970 Review. - Quorum Sensing Inhibitors: An Alternative Strategy to Win the Battle against Multidrug-Resistant (MDR) Bacteria.
Hetta HF, Ramadan YN, Rashed ZI, Alharbi AA, Alsharef S, Alkindy TT, Alkhamali A, Albalawi AS, Battah B, Donadu MG. Hetta HF, et al. Molecules. 2024 Jul 24;29(15):3466. doi: 10.3390/molecules29153466. Molecules. 2024. PMID: 39124871 Free PMC article. Review. - Microbial metabolomics' latest SICRIT: Soft ionization by Chemical Reaction in-Transfer mass spectrometry.
McAtamney A, Ferranti A, Ludvik DA, Yildiz FH, Mandel MJ, Hayward T, Sanchez LM. McAtamney A, et al. bioRxiv [Preprint]. 2024 Jul 18:2024.07.17.604007. doi: 10.1101/2024.07.17.604007. bioRxiv. 2024. PMID: 39071417 Free PMC article. Updated. Preprint. - Lighting the way: how the Vibrio fischeri model microbe reveals the complexity of Earth's "simplest" life forms.
Septer AN, Visick KL. Septer AN, et al. J Bacteriol. 2024 May 23;206(5):e0003524. doi: 10.1128/jb.00035-24. Epub 2024 May 2. J Bacteriol. 2024. PMID: 38695522 Free PMC article. Review. - Insights into additional lactone-based signaling circuits in Streptomyces: existence of acyl-homoserine lactones and LuxI/LuxR homologs in six Streptomyces species.
Salehi-Najafabadi A, Tehrani Fateh S, Amoabediny G, Hamedi J. Salehi-Najafabadi A, et al. Front Microbiol. 2024 Feb 8;15:1342637. doi: 10.3389/fmicb.2024.1342637. eCollection 2024. Front Microbiol. 2024. PMID: 38389542 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Other Literature Sources
Molecular Biology Databases