The hydrolysis of unsubstituted N-acylhomoserine lactones to their homoserine metabolites. Analytical approaches using ultra performance liquid chromatography

Matthias Englmann, Agnes Fekete, Christina Kuttler, Moritz Frommberger, Xiaojing Li, Istvan Gebefügi, Jenoe Fekete, Philippe Schmitt-Kopplin

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Derivatives of N-acylhomoserine lactones (HSLs) with different alkanoyl side chains occur as quorum or diffusion sensing molecules in Gram-negative bacteria and their quantitative chemical analysis became important as a possible way to follow regulation processes of their pathogenicity towards plants and animals. The lactone-ring of HSLs is chemically and biologically not stable: the corresponding serines can be formed in alkaline conditions and these may presumably behave inactive for the biological system. A fast and MS compatible liquid chromatographic method applying high pressure (ultra performance liquid chromatography) with diode array detection was optimized for the rapid quantitative determination of HSLs and their corresponding hydrolysis products. The technique was used to follow and model the hydrolysis reactions of HSLs as function of pH under controlled conditions. Moreover, the method could be triggered to allow a confirmation in the assignment of the potential HSLs in real samples by analysis of the real samples before and after hydrolysis. Quantitative performance characteristics and the character of the hydrolysis reaction were studied as well. The optimized method was successfully applied to a bacterial culture supernatant real sample containing HSLs.

Original languageEnglish
Pages (from-to)184-193
Number of pages10
JournalJournal of Chromatography A
Volume1160
Issue number1-2
DOIs
Publication statusPublished - Aug 10 2007

Keywords

  • Hydrolysis
  • N-acylhomoserine lactones
  • N-acylhomoserines
  • Optimization
  • Quorum sensing
  • UPLC

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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