1. Structural characterization of N-acyl-homoserine lactones from bacterial quorum sensing using LC–MS/MS analyses after Paternò-Büchi derivatization in solution.
- Author
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Gosset-Erard, Clarisse, Han, Guanghui, Kyrko, Dimitra, Hueber, Amandine, Nay, Bastien, Eparvier, Véronique, and Touboul, David
- Subjects
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TANDEM mass spectrometry , *QUORUM sensing , *DOUBLE bonds , *MATRIX effect , *GRAM-negative bacteria - Abstract
Bacterial quorum sensing is a chemical language allowing bacteria to interact through the excretion of molecules called autoinducers, like N-acyl-homoserine lactones (AHLs) produced by Gram-negative Burkholderia and Paraburkholderia bacteria known as opportunistic pathogens. The AHLs differ in their acyl-chain length and may be modified by a 3-oxo or 3-hydroxy substituent, or C = C double bonds at different positions. As the bacterial signal specificity depends on all of these chemical features, their structural characterization is essential to have a better understanding of the population regulation and virulence phenomenon. This study aimed at enabling the localization of the C = C double bond on such specialized metabolites while using significantly lower amounts of biological material. The approach is based on LC–MS/MS analyses of bacterial extracts after in-solution derivatization by a photochemical Paternò-Büchi reaction, leading to the formation of an oxetane ring and subsequently to specific fragmentations when performing MS/MS experiments. The in-solution derivatization of AHLs was optimized on several standards, and then the matrix effect of bacterial extracts on the derivatization was assessed. As a proof of concept, the optimized conditions were applied to a bacterial extract enabling the localization of C = C bonds on unsaturated AHLs. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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