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Synthesis and analysis of stable isotope-labelled N-acyl homoserine lactones

Ewout Ruysbergh (UGent) , Christian Stevens (UGent) , Norbert De Kimpe (UGent) and Sven Mangelinckx (UGent)
(2016) RSC ADVANCES. 6(77). p.73717-73730
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BOF 14/DOC_V/285
Abstract
Aliphatic aldehydes were deuterated at the alpha-position via a base-catalyzed exchange reaction with D2O. These deuterated building blocks were used for the synthesis of labelled analogues of quorum sensing signal molecules belonging to the three major classes of naturally occurring N-acylated homoserine lactones (AHLs), with the label on a non-enolizable and therefore stable position. Besides the application of these stable isotope-labelled AHLs as a labelled standard for analysis via isotope dilution mass spectrometry, these compounds can be used to study the metabolic fate of the fatty acid tail of the AHL-molecule. These isotope-labelled compounds were fully characterized and used to synthesize the deuterated analogues of two commonly occurring AHL-degradation products, a tetramic acid and a ring opened N-acyl homoserine.
Keywords
QUORUM-SENSING SIGNALS, CHROMATOGRAPHY-MASS SPECTROMETRY, SOLID-PHASE EXTRACTION, GRAM-NEGATIVE BACTERIA, LINEAR ION-TRAP, LTQ-FTICR-MS, ACYLHOMOSERINE LACTONES, LIQUID-CHROMATOGRAPHY, PSEUDOMONAS-AERUGINOSA, YERSINIA-PSEUDOTUBERCULOSIS

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Citation

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Chicago
Ruysbergh, Ewout, Christian Stevens, Norbert De Kimpe, and Sven Mangelinckx. 2016. “Synthesis and Analysis of Stable Isotope-labelled N-acyl Homoserine Lactones.” Rsc Advances 6 (77): 73717–73730.
APA
Ruysbergh, E., Stevens, C., De Kimpe, N., & Mangelinckx, S. (2016). Synthesis and analysis of stable isotope-labelled N-acyl homoserine lactones. RSC ADVANCES, 6(77), 73717–73730.
Vancouver
1.
Ruysbergh E, Stevens C, De Kimpe N, Mangelinckx S. Synthesis and analysis of stable isotope-labelled N-acyl homoserine lactones. RSC ADVANCES. 2016;6(77):73717–30.
MLA
Ruysbergh, Ewout, Christian Stevens, Norbert De Kimpe, et al. “Synthesis and Analysis of Stable Isotope-labelled N-acyl Homoserine Lactones.” RSC ADVANCES 6.77 (2016): 73717–73730. Print.
@article{8150433,
  abstract     = {Aliphatic aldehydes were deuterated at the alpha-position via a base-catalyzed exchange reaction with D2O. These deuterated building blocks were used for the synthesis of labelled analogues of quorum sensing signal molecules belonging to the three major classes of naturally occurring N-acylated homoserine lactones (AHLs), with the label on a non-enolizable and therefore stable position. Besides the application of these stable isotope-labelled AHLs as a labelled standard for analysis via isotope dilution mass spectrometry, these compounds can be used to study the metabolic fate of the fatty acid tail of the AHL-molecule. These isotope-labelled compounds were fully characterized and used to synthesize the deuterated analogues of two commonly occurring AHL-degradation products, a tetramic acid and a ring opened N-acyl homoserine.},
  author       = {Ruysbergh, Ewout and Stevens, Christian and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {2046-2069},
  journal      = {RSC ADVANCES},
  keyword      = {QUORUM-SENSING SIGNALS,CHROMATOGRAPHY-MASS SPECTROMETRY,SOLID-PHASE EXTRACTION,GRAM-NEGATIVE BACTERIA,LINEAR ION-TRAP,LTQ-FTICR-MS,ACYLHOMOSERINE LACTONES,LIQUID-CHROMATOGRAPHY,PSEUDOMONAS-AERUGINOSA,YERSINIA-PSEUDOTUBERCULOSIS},
  language     = {eng},
  number       = {77},
  pages        = {73717--73730},
  title        = {Synthesis and analysis of stable isotope-labelled N-acyl homoserine lactones},
  url          = {http://dx.doi.org/10.1039/c6ra17797b},
  volume       = {6},
  year         = {2016},
}

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