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Structure and Biosynthesis of Isatropolones, Bioactive Amine-Scavenging Fluorescent Natural Products from Streptomyces Gö66.
Journal article

Structure and Biosynthesis of Isatropolones, Bioactive Amine-Scavenging Fluorescent Natural Products from Streptomyces Gö66.

  • Cai X Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
  • Shi YM Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
  • Pöhlmann N Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Germany.
  • Revermann O Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Germany.
  • Bahner I Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Germany.
  • Pidot SJ Department of Microbiology and Immunology, The Peter Doherty Institute for Infection and Immunity, The University of Melbourne, Australia.
  • Wesche F Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
  • Lackner H Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Germany.
  • Büchel C Institute of Molecular Biosciences, Goethe-Universität Frankfurt, Germany.
  • Kaiser M Swiss Tropical and Public Health Institute, Parasite Chemotherapy, Basel, Switzerland.
  • Richter C Institut für Organische Chemie und Chemische Biologie, Zentrum für Biomolekulare Magnetische Resonanz, Goethe-Universität Frankfurt, Germany.
  • Schwalbe H Institut für Organische Chemie und Chemische Biologie, Zentrum für Biomolekulare Magnetische Resonanz, Goethe-Universität Frankfurt, Germany.
  • Stinear TP Department of Microbiology and Immunology, The Peter Doherty Institute for Infection and Immunity, The University of Melbourne, Australia.
  • Zeeck A Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Germany.
  • Bode HB Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
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  • 2017-04-04
Published in:
  • Angewandte Chemie (International ed. in English). - 2017
1,5-diketones
fluorescence
isatropolones
natural products
rubrolones
Amines
Animals
Antiparasitic Agents
Biological Products
Biosynthetic Pathways
Cell Line
Fluorescent Dyes
Humans
Leishmania donovani
Leishmaniasis, Visceral
Multigene Family
Rats
Streptomyces
Tropolone
English The natural products isatropolone A-C (1-3) were reisolated from Streptomyces Gö66, with 1 and 3 showing potent activity against Leishmania donovani. They contain a rare tropolone ring derived from a type II polyketide biosynthesis pathway. Their biosynthesis was elucidated by labeling experiments, analysis of the biosynthesis gene cluster, its partial heterologous expression, and structural characterization of various intermediates. Owing to their 1,5-diketone moiety, they can react with ammonia, amines, lysine, and lysine-containing peptides and proteins, which results in the formation of a covalent bond and subsequent pyridine ring formation. Their fluorescence properties change upon amine binding, enabling the simple visualization of reacted amines including proteins.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/224673
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