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Identification of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone by reversed-phase high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.

Publication ,  Journal Article
Cui, Y; Frey, RL; Ferry, JL; Ferguson, PL
Published in: Rapid communications in mass spectrometry : RCM
April 2009

A reversed-phase high-performance liquid chromatography/electrospray tandem mass spectrometry method was developed for the characterization of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone (C6-HSL), a member of the N-acylhomoserine lactone (AHL) class of microbial quorum-sensing signaling molecules identified in many Gram-negative strains of bacteria. Six products were identified: four with molecular weight (MW) of 213 and two with MW of 260. The characteristic product ions formed through collision-induced dissociation (CID) provided diagnostic structural information. One of the photolysis products was determined to be N-(3-oxohexanoyl)homoserine lactone (3OC6-HSL), a highly active quorum-sensing signal, by comparison with a reference standard. Three structural isomers with the same mass as 3OC6-HSL were identified as acyl side chain oxidized C6-HSL (keto/enol functionalized) by accurate mass measurement and the structures of these products were proposed from CID spectral interpretation. Two structural isomers formed from concurrent oxidation and nitration of C6-HSL were also observed and their structures were postulated based on CID spectra. In addition to the six hydroxyl radical oxidation products formed from the C6-HSL precursor, five additional compounds generated from combined oxidation and lactonolysis of C6-HSL were identified and structures were postulated.

Duke Scholars

Published In

Rapid communications in mass spectrometry : RCM

DOI

EISSN

1097-0231

ISSN

0951-4198

Publication Date

April 2009

Volume

23

Issue

8

Start / End Page

1212 / 1220

Related Subject Headings

  • Tandem Mass Spectrometry
  • Oxidation-Reduction
  • Molecular Structure
  • Hydroxyl Radical
  • Hydrogen-Ion Concentration
  • Chromatography, High Pressure Liquid
  • Analytical Chemistry
  • 4-Butyrolactone
  • 37 Earth sciences
  • 34 Chemical sciences
 

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Cui, Y., Frey, R. L., Ferry, J. L., & Ferguson, P. L. (2009). Identification of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone by reversed-phase high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 23(8), 1212–1220. https://doi.org/10.1002/rcm.3991
Cui, Yiling, Rebecca L. Frey, John L. Ferry, and P Lee Ferguson. “Identification of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone by reversed-phase high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.Rapid Communications in Mass Spectrometry : RCM 23, no. 8 (April 2009): 1212–20. https://doi.org/10.1002/rcm.3991.
Cui, Yiling, et al. “Identification of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone by reversed-phase high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.Rapid Communications in Mass Spectrometry : RCM, vol. 23, no. 8, Apr. 2009, pp. 1212–20. Epmc, doi:10.1002/rcm.3991.
Journal cover image

Published In

Rapid communications in mass spectrometry : RCM

DOI

EISSN

1097-0231

ISSN

0951-4198

Publication Date

April 2009

Volume

23

Issue

8

Start / End Page

1212 / 1220

Related Subject Headings

  • Tandem Mass Spectrometry
  • Oxidation-Reduction
  • Molecular Structure
  • Hydroxyl Radical
  • Hydrogen-Ion Concentration
  • Chromatography, High Pressure Liquid
  • Analytical Chemistry
  • 4-Butyrolactone
  • 37 Earth sciences
  • 34 Chemical sciences