The first total synthesis of the heptapeptide Cyclomarin A (CymA) was achieved via new routes to chiral amino acid building blocks (highlighted) and solid-phase peptide synthesis. A structurally misassigned epimer of CymA (CymA'), Cyclomarin C, and Metamarin were also synthesized. Affirmation of the syntheses was corroborated by observations that the synthetic molecules have antimicrobial activities mirroring those of the natural products. Interestingly, CymA' is more potent than CymA.
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http://dx.doi.org/10.1021/acs.orglett.4c03473 | DOI Listing |
Org Lett
November 2024
Department of Pharmaceutical Chemistry, University of California, San Francisco, California 94143, United States.
The first total synthesis of the heptapeptide Cyclomarin A (CymA) was achieved via new routes to chiral amino acid building blocks (highlighted) and solid-phase peptide synthesis. A structurally misassigned epimer of CymA (CymA'), Cyclomarin C, and Metamarin were also synthesized. Affirmation of the syntheses was corroborated by observations that the synthetic molecules have antimicrobial activities mirroring those of the natural products.
View Article and Find Full Text PDFJ Nat Prod
April 2021
Laboratory of Genetically Encoded Small Molecules, The Rockefeller University, 1230 York Avenue, New York, New York 10065, United States.
Tuberculosis (TB) remains one of the deadliest infectious diseases. Unfortunately, the development of antibiotic resistance threatens our current therapeutic arsenal, which has necessitated the discovery and development of novel antibiotics against drug-resistant (). Cyclomarin A and rufomycin I are structurally related cyclic heptapeptides assembled by nonribosomal peptide synthetases (NRPSs), which show potent anti- activity with a new cellular target, the caseinolytic protein ClpC1.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!