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Total Synthesis of the Reported Structure of Cahuitamycin A

preprint
submitted on 23.07.2020 and posted on 24.07.2020 by Justin Shapiro, Savannah Post, William Wuest
In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen Acinetobacter baumannii. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from A. baumannii, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Funding

GM119426

GM133091

DGE1937971

History

Email Address of Submitting Author

wwuest@emory.edu

Institution

Emory University

Country

United States

ORCID For Submitting Author

0000-0002-5198-7744

Declaration of Conflict of Interest

no conflict of interest

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