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  Comparative ascaroside profiling of Caenorhabditis exometabolomes reveals species-specific (omega) and (omega – 2)-hydroxylation downstream of peroxisomal beta-oxidation

Dong, C.-F., Reilly, D. K., Bergame, C., Dolke, F., Srinivasan, J., & von Reuss, S. H. (2018). Comparative ascaroside profiling of Caenorhabditis exometabolomes reveals species-specific (omega) and (omega – 2)-hydroxylation downstream of peroxisomal beta-oxidation. The Journal of Organic Chemistry, 83(13), 7109-7120. doi:10.1021/acs.joc.8b00094.

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BOL694s1.pdf (Supplementary material), 14MB
 
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Dong, Chuan-Fu1, Author           
Reilly, Douglas K., Author
Bergame, Célia, Author
Dolke, Franziska1, 2, Author           
Srinivasan, Jagan, Author
von Reuss, Stephan H.1, Author           
Affiliations:
1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              

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 Abstract: Chemical communication in nematodes, such as the model organism Caenorhabditis elegans, is modulated by a variety of glycosides based on the dideoxysugar L-ascarylose. Comparative ascaroside profiling of nematode exometabolome extracts using a GC-EIMS screen reveals that several basic components including ascr#1 (asc-C7), ascr#2 (asc-C6-MK), ascr#3 (asc- DC9), ascr#5 (asc-ωC3), and ascr#10 (asc-C9) are highly conserved among the Caenorhabditis. Three novel, side chain hydroxylated ascaroside derivatives were exclusively detected in the distantly related C. nigoni and C. afra. Molecular structures of these speciesspecific, putative signaling molecules were elucidated by NMR spectroscopy and confirmed by total synthesis and chemical correlations. Biological activities were evaluated using attraction assays. The identification of (ω)- and (ω – 2)-hydroxyacyl ascarosides demonstrates how GC-EIMS-based ascaroside profiling facilitates the detection of novel ascaroside components and exemplifies how species-specific hydroxylation of ascaroside aglycones downstream of peroxisomal β-oxidation increases the structural diversity of this highly conserved class of nematode signaling molecules.

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 Dates: 2018-02-262018-03-052018-07
 Publication Status: Published in print
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 Identifiers: Other: BOL694
DOI: 10.1021/acs.joc.8b00094
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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 83 (13) Sequence Number: - Start / End Page: 7109 - 7120 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1