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Org Lett. 2019 Nov 1;21(21):8731-8735. doi: 10.1021/acs.orglett.9b03348. Epub 2019 Oct 21.

Total Synthesis of the Bacterial Diisonitrile Chalkophore SF2768.

Abstract

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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