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Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry

Verena Thiel, Ramiro Vilchez Vargas (UGent) , Helena Sztajer, Irene Wagner-Döbler and Stefan Schulz
(2009) CHEMBIOCHEM. 10(3). p.479-485
Author
Organization
Abstract
Autoinducer-2 (AI-2) is on important, small extracellular signaling molecule that is used by many bacteria. It is part of the AI-2 pool, a group of equilibrium-connected compounds derived from (S)-4,5-dihydroxy-2,3-pentanedione [(S)-DPD, 1]. Currently, these compounds are analyzed by indirect methods relying on the luminescence of sensor strains, the fluorescence of receptor proteins modified with fluorophores, or by isolation procedures not practical for quantitative analysis. Herein, we report a direct analytical procedure that allows for the unambiguous identification and quantification of molecular species by mass spectrometry. Phenylenediamine reacts readily and quantitatively with 1 to form the quinoxalinediol 12 under aqueous conditions. The extraction and silylation of this compound results in the formation of a silyl ether (13), which is amenable for analysis by gas chromatography-mass spectrometry. The use of an isotopically labeled variant (16) of 12 as an internal standard opens the possibility for the accurate quantification of samples containing AI-2 or its equilibrium products. The analysis of cell-free culture supernatants of Vibrio harveyi and Streptococcus mutans allowed for the accurate quantification of the AI-2 concentration above the limit of detection (0.7 ng mL(-1)). No compounds were detected in mutants locking the capability to produce AI-2. In addition, the absolute configuration of 1 can be analyzed using the derivative 13 by chiral gas chromatography.
Keywords
MARINE-BACTERIA, LUXS, STREPTOCOCCUS-MUTANS, SALMONELLA-TYPHIMURIUM, VIBRIO-HARVEYI, quorum sensing, carbohydrates, pheromones, gas chromatography, mass spectrometry, BIOSYNTHESIS, LUMINESCENCE, VALIDATION, EXPRESSION, INDUCTION

Citation

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MLA
Thiel, Verena, et al. “Identification, Quantification, and Determination of the Absolute Configuration of the Bacterial Quorum-Sensing Signal Autoinducer-2 by Gas Chromatography-Mass Spectrometry.” CHEMBIOCHEM, vol. 10, no. 3, 2009, pp. 479–85, doi:10.1002/cbic.200800606.
APA
Thiel, V., Vilchez Vargas, R., Sztajer, H., Wagner-Döbler, I., & Schulz, S. (2009). Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry. CHEMBIOCHEM, 10(3), 479–485. https://doi.org/10.1002/cbic.200800606
Chicago author-date
Thiel, Verena, Ramiro Vilchez Vargas, Helena Sztajer, Irene Wagner-Döbler, and Stefan Schulz. 2009. “Identification, Quantification, and Determination of the Absolute Configuration of the Bacterial Quorum-Sensing Signal Autoinducer-2 by Gas Chromatography-Mass Spectrometry.” CHEMBIOCHEM 10 (3): 479–85. https://doi.org/10.1002/cbic.200800606.
Chicago author-date (all authors)
Thiel, Verena, Ramiro Vilchez Vargas, Helena Sztajer, Irene Wagner-Döbler, and Stefan Schulz. 2009. “Identification, Quantification, and Determination of the Absolute Configuration of the Bacterial Quorum-Sensing Signal Autoinducer-2 by Gas Chromatography-Mass Spectrometry.” CHEMBIOCHEM 10 (3): 479–485. doi:10.1002/cbic.200800606.
Vancouver
1.
Thiel V, Vilchez Vargas R, Sztajer H, Wagner-Döbler I, Schulz S. Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry. CHEMBIOCHEM. 2009;10(3):479–85.
IEEE
[1]
V. Thiel, R. Vilchez Vargas, H. Sztajer, I. Wagner-Döbler, and S. Schulz, “Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry,” CHEMBIOCHEM, vol. 10, no. 3, pp. 479–485, 2009.
@article{4421161,
  abstract     = {{Autoinducer-2 (AI-2) is on important, small extracellular signaling molecule that is used by many bacteria. It is part of the AI-2 pool, a group of equilibrium-connected compounds derived from (S)-4,5-dihydroxy-2,3-pentanedione [(S)-DPD, 1]. Currently, these compounds are analyzed by indirect methods relying on the luminescence of sensor strains, the fluorescence of receptor proteins modified with fluorophores, or by isolation procedures not practical for quantitative analysis. Herein, we report a direct analytical procedure that allows for the unambiguous identification and quantification of molecular species by mass spectrometry. Phenylenediamine reacts readily and quantitatively with 1 to form the quinoxalinediol 12 under aqueous conditions. The extraction and silylation of this compound results in the formation of a silyl ether (13), which is amenable for analysis by gas chromatography-mass spectrometry. The use of an isotopically labeled variant (16) of 12 as an internal standard opens the possibility for the accurate quantification of samples containing AI-2 or its equilibrium products. The analysis of cell-free culture supernatants of Vibrio harveyi and Streptococcus mutans allowed for the accurate quantification of the AI-2 concentration above the limit of detection (0.7 ng mL(-1)). No compounds were detected in mutants locking the capability to produce AI-2. In addition, the absolute configuration of 1 can be analyzed using the derivative 13 by chiral gas chromatography.}},
  author       = {{Thiel, Verena and Vilchez Vargas, Ramiro and Sztajer, Helena and Wagner-Döbler, Irene and Schulz, Stefan}},
  issn         = {{1439-4227}},
  journal      = {{CHEMBIOCHEM}},
  keywords     = {{MARINE-BACTERIA,LUXS,STREPTOCOCCUS-MUTANS,SALMONELLA-TYPHIMURIUM,VIBRIO-HARVEYI,quorum sensing,carbohydrates,pheromones,gas chromatography,mass spectrometry,BIOSYNTHESIS,LUMINESCENCE,VALIDATION,EXPRESSION,INDUCTION}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{479--485}},
  title        = {{Identification, quantification, and determination of the absolute configuration of the bacterial quorum-sensing signal autoinducer-2 by gas chromatography-mass spectrometry}},
  url          = {{http://doi.org/10.1002/cbic.200800606}},
  volume       = {{10}},
  year         = {{2009}},
}
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