Synthesis of the trans-fusarinine scaffold |
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Authors: | Samuel Bertrand,Jean-Jacques Hé lesbeux,Pascal Richomme |
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Affiliation: | a Laboratoire des Substances d’Origine Naturelle et Analogues Structuraux, UPRES-EA 921, IFR 149 QUASAV, UFR des Sciences Pharmaceutiques et Ingénierie de la Santé, Université d’Angers, 16 Bd Daviers, 49045 Angers Cedex, France b Groupe d’Etude des Interactions Hôte-Parasite, UPRES-EA 3142, IFR 132, UFR des Sciences Pharmaceutiques et Ingénierie de la Santé, Université d’Angers, 16 Bd Daviers, 49045 Angers Cedex, France |
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Abstract: | The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of Nα-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from l-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone. |
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Keywords: | Siderophore Fusarinine Multi-step synthesis |
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