Analytical and Bioanalytical Chemistry

, Volume 387, Issue 2, pp 455–467

Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors

  • Agnes Fekete
  • Moritz Frommberger
  • Michael Rothballer
  • Xiaojing Li
  • Matthias Englmann
  • Jenoe Fekete
  • Anton Hartmann
  • Leo Eberl
  • Philippe Schmitt-Kopplin
Review

DOI: 10.1007/s00216-006-0970-8

Cite this article as:
Fekete, A., Frommberger, M., Rothballer, M. et al. Anal Bioanal Chem (2007) 387: 455. doi:10.1007/s00216-006-0970-8

Abstract

N-Acylated homoserine lactones (AHLs) are produced by Gram-negative bacteria as communication signals and are frequently studied as mediators of the “quorum sensing” response of bacterial communities. Several reports have recently been published on the identification of AHLs from different species and attempts have been made to study their role in natural habitats, for example the surface of plant roots in the rhizosphere. In this article, different analytical methods, including bacterial biosensors and chromatographic techniques, are reviewed. A concept for assignment of the structures of AHLs is also presented. The retention behaviour of derivatives of AHLs containing β-keto or hydroxyl groups and/or double bonds has been evaluated in relation to the separation behaviour of AHLs with saturated and unsubstituted alkanoyl chains. Samples have also been analysed by high resolution mass spectrometry (Fourier-transform ion-cyclotron-resonance mass spectrometry, FTICR-MS), nano liquid chromatography–electrospray ionization ion trap mass spectrometry (nano-LC–MS) and by the aid of a biosensor. The results obtained from ultra performance liquid chromatography (UPLC), FTICR-MS, nano-LC–MS, and bioassays have been compared to attempt structural characterisation of AHL without chemical synthesis of analytical standards. The method was used to identify the major AHL compound produced by the rhizosphere bacterium Acidovorax sp. N35 as N-(3-hydroxydecanoyl)homoserine lactone.

Keywords

N-Acylhomoserine lactones Biosensing Chromatography UPLC FTICR-MS 

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  • Agnes Fekete
    • 1
  • Moritz Frommberger
    • 1
  • Michael Rothballer
    • 2
  • Xiaojing Li
    • 1
    • 3
  • Matthias Englmann
    • 1
  • Jenoe Fekete
    • 4
  • Anton Hartmann
    • 2
  • Leo Eberl
    • 5
  • Philippe Schmitt-Kopplin
    • 1
  1. 1.Institute of Ecological ChemistryGSF - National Research Center for Environment and HealthNeuherbergGermany
  2. 2.Department of Rhizosphere Biology, Institute of Soil EcologyGSF - National Research Center for Environment and HealthNeuherbergGermany
  3. 3.Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety and Department of ChemistryFuzhou UniversityFuzhouChina
  4. 4.Department of General and Analytical ChemistryFaculty of Chemical Engineering, Budapest University of Technology and EconomicsBudapestHungary
  5. 5.Department of MicrobiologyUniversity of ZürichZürichSwitzerland

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