Total Synthesis of the Bacterial Diisonitrile ChalkophoreSF2768
2019
Chalkophores are bacterial natural
products that chelate and transport extracellular copper. The diisonitrile
natural product SF2768 was first isolated from a Streptomyces species as an antifungal antibiotic and has more recently been characterized
as a bacterial chalkophore and potential virulence factor. Herein,
we report a modular synthesis of SF2768 and related acyclic analogues,
allowing assignment of syn-stereochemistry across
the central lactol ring. The copper-binding properties of these diisonitriles
have also been studied.
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