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  Ascaroside profiling of Caenorhabditis elegans using gas chromatography-electron ionization mass spectrometry

von Reuss, S. H., Dolke, F., & Dong, C.-F. (2017). Ascaroside profiling of Caenorhabditis elegans using gas chromatography-electron ionization mass spectrometry. Analytical Chemistry, 89(19), 10570-10577. doi:10.1021/acs.analchem.7b02803.

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von Reuss, Stephan H.1, Author              
Dolke, Franziska1, Author              
Dong, Chuan-Fu1, Author              
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1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              

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 Abstract: Nematodes such as the model organism Caenorhabditis elegans produce homologous series of L-ascarylose-derived glyco-lipids called ascarosides, which include several highly potent signals in intra and interspecies communication as well as cross-kingdom interactions. Given their low concentrations and large number of structurally similar components, mass spectrometric screens based on HPLC-ESI-MS/MS are commonly employed for ascaroside detection and quantification. Here, we describe a complementary GC-EIMS screen that utilizes an ascarylose-derived K1-fragment ion signal at m/z 130.1 [C6H14OSi]+● to highlight known as well as yet unidentified ascaroside components in TMS-derivatized crude nematode exo-metabolome extracts. GC-EIMS-based ascaroside profiling of wild-type and mutant C. elegans facilitates the analysis of all basic ascarosides using the same ionization technique while providing excellent resolution for the complete homologous series with sidechains ranging from 3 to 33 carbons. Combined screening for m/z 130.1 along with sidechain-specific J1 [M-173] and J2 [M-291] fragment ions, as well as additional characteristic marker ions from α-cleavage, enables convenient structure assignment of ca. 200 components from wild-type and peroxisomal β-oxidation mutants including (ω-1)-linked acyl, enoyl, β-hydroxyacyl and 2-ketoalkyl ascarosides along with their (ω)-linked or α-methyl isomers and ethanolamide derivatives, as well as 2-hydroxyalkyl ascarosides. Given the widespread availability of GC-MS and its increasing popularity in metabolomics this method will promote the identification of ascarosides in C. elegans and other nematodes.

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 Dates: 2017-09-042017-10-03
 Publication Status: Published online
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 Identifiers: Other: BOL683
DOI: 10.1021/acs.analchem.7b02803
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Title: Analytical Chemistry
  Abbreviation : Anal. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 89 (19) Sequence Number: - Start / End Page: 10570 - 10577 Identifier: ISSN: 0003-2700
CoNE: https://pure.mpg.de/cone/journals/resource/111032812862552