Single drop microextraction of homoserine lactones based quorum sensing signal molecules, and the separation of their enantiomers using gas chromatography mass spectrometry in the presence of biological matrices |
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Authors: | Ashok Kumar Malik Agnes Fekete Istvan Gebefuegi Michael Rothballer Philippe Schmitt-Kopplin |
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Institution: | 1. Institute of Ecological Chemistry, HelmholtzZentrum Muenchen, Research Center for Environment and Health, Ingolst?dter Landstra?e 1, D-85764, Neuherberg, Germany 2. Department of Chemistry, Punjabi University, Patiala-147 002, Punjab, India 3. Department of Microbe-Plant Interactions, HelmholtzZentrum Muenchen, Research Center for Environment and Health, Ingolst?dter Landstra?e 1, D-85764, Neuherberg, Germany
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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. AHLs are optically active components and the L-form is known to have activity in the quorum sensing. However, the knowledge regarding the stereospecific production of the AHLs in bacterial cultures is limited; therefore, there is a need for a fast and easy method for their chiral analysis. A method was developed for the preconcentration of the AHLs using single drop microextraction or liquid-liquid microphase extraction in toluene for their analysis using GC-MS. The performance of the method were determined and discussed for the chiral separation of these autoinducers using a capillary column coated with heptakis-(2,3-di-O-acetyl-6-O-t-butyldimethyl-silyl)-β-cyclodextrin. The salient feature of this study is the demonstration, that Burkholderia cepacia LA3 produced D-decanoyl-homoserine lactone beside L-decanoyl- and L-octaonyl- enantiomers. |
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