A Sweet Origin for the Key Congocidine Precursor 4-Acetamidopyrrole-2-carboxylate

Authors

  • Dr. Sylvie Lautru,

    Corresponding author
    1. Institut de Génétique et Microbiologie, Université Paris-Sud, CNRS, UMR8621, 91405 Orsay (France)
    • Institut de Génétique et Microbiologie, Université Paris-Sud, CNRS, UMR8621, 91405 Orsay (France)
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  • Dr. Lijiang Song,

    1. Department of Chemistry, University of Warwick, Coventry CV4 7AL (UK)
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  • Dr. Luc Demange,

    1. Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques UMR 8601 CNRS, Université Paris Descartes, Sorbonne Paris Cité, UFR Biomédicale des Saints Pères, 45 rue des Saints Pères, 75006 Paris (France)
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  • Thomas Lombès,

    1. UMR 8638 CNRS-Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av. de l'Observatoire, 75006 Paris (France)
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  • Prof. Hervé Galons,

    1. Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques UMR 8601 CNRS, Université Paris Descartes, Sorbonne Paris Cité, UFR Biomédicale des Saints Pères, 45 rue des Saints Pères, 75006 Paris (France)
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  • Prof. Gregory L. Challis,

    1. Department of Chemistry, University of Warwick, Coventry CV4 7AL (UK)
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  • Dr. Jean-Luc Pernodet

    1. Institut de Génétique et Microbiologie, Université Paris-Sud, CNRS, UMR8621, 91405 Orsay (France)
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  • We would like to thank Dr. Christophe Corre for helpful discussions, Dr. Laurent Micouin for his help with the synthesis of the 4-acetamidopyrrole-2-methanol, and Dr. Cyrille Kouklovsky, Géraldine Le Goff, and Dr. Robert Thaï for their help with mass spectrometry. This work was supported in part by the European Union through the Integrated Project ActinoGEN (CT-2004-0005224) and the reintegration grant BOPA (CT-2005-029154), by the Pôle de Recherche et d’Enseignement Supérieur UniverSud Paris and by the Bettencourt Schueller Foundation.

Abstract

original image

Charakteristisch für Pyrrolamid-Naturstoffe ist eine Pyrrol-2-carboxamid-Einheit. In Fütterungsexperimenten mit Streptomyces ambofaciens wurde 4-Acetamidopyrrol-2-carboxylat als die entscheidende Pyrrolamid-Vorstufe von Congocidin identifiziert (siehe Schema). Die Biosynthese von Congocidin geht von N-Acetylglucosamin aus und verläuft unter Beteiligung von Enzymen, die Kohlenhydrate umsetzen.

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