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  Comparative metabolomics reveals biogenesis of ascarosides, a modular library of small-molecule signals in C. elegans

von Reuß, S. H., Bose, N., Srinivasan, J., Yim, J. J., Judkins, J. C., Sternberg, P. W., et al. (2012). Comparative metabolomics reveals biogenesis of ascarosides, a modular library of small-molecule signals in C. elegans. Journal of the American Chemical Society, 134(3), 1817-1824. doi:10.1021/ja210202y.

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 Urheber:
von Reuß, Stephan H.1, Autor           
Bose, Neelanjan, Autor
Srinivasan, Jagan, Autor
Yim, Joshua J., Autor
Judkins, Joshua C., Autor
Sternberg, Paul W., Autor
Schroeder, Frank C., Autor
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1External Organizations, ou_persistent22              

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 Zusammenfassung: In the model organism Caenorhabditis elegans, a family of endogenous small molecules, the ascarosides function as key regulators of developmental timing and behavior that act upstream of conserved signaling pathways. The ascarosides are based on the dideoxysugar ascarylose, which is linked to fatty-acid-like side chains of varying lengths derived from peroxisomal beta-oxidation. Despite the importance of ascarosides for many aspects of C. elegans biology, knowledge of their structures, biosynthesis, and homeostasis remains incomplete. We used an MS/MS-based screen to profile ascarosides in C. elegans wild-type and mutant metabolomes, which revealed a much greater structural diversity of ascaroside derivatives than previously reported. Comparison of the metabolomes from wildtype and a series of peroxisomal beta-oxidation mutants showed that the enoyl CoA-hydratase MAOC-1 serves an important role in ascaroside biosynthesis and clarified the functions of two other enzymes, ACOX-1 and DHS-28. We show that, following peroxisomal beta-oxidation, the ascarosides are selectively derivatized with moieties of varied biogenetic origin and that such modifications can dramatically affect biological activity, producing signaling molecules active at low femtomolar concentrations. Based on these results, the ascarosides appear as a modular library of small-molecule signals, integrating building blocks from three major metabolic pathways: carbohydrate metabolism, peroxisomal beta-oxidation of fatty acids, and amino acid catabolism. Our screen further demonstrates that ascaroside biosynthesis is directly affected by nutritional status and that excretion of the final products is highly selective.

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 Datum: 2012
 Publikationsstatus: Online veröffentlicht
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 Identifikatoren: Anderer: EXT076
DOI: 10.1021/ja210202y
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Titel: Journal of the American Chemical Society
  Andere : J. Am. Chem. Soc.
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: American Chemical Society
Seiten: - Band / Heft: 134 (3) Artikelnummer: - Start- / Endseite: 1817 - 1824 Identifikator: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870