Total Synthesis of the Bacterial Diisonitrile Chalkophore SF2768

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


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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Chemistry Techniques, Synthetic
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry*
  • Streptomyces / chemistry*


  • Nitriles