Totopotensamides, Polyketide–Cyclic Peptide Hybrids from a Mollusk-Associated Bacterium Streptomyces sp.

Zhenjian Lin†, Malem Flores‡, Imelda Forteza‡, Niel M. Henriksen†, Gisela P. Concepcion‡, Gary Rosenberg§, Margo G. Haygood, Baldomero M. Olivera, Alan R. Light, Thomas E. Cheatham, III†, and Eric W. Schmidt*†
† College of Pharmacy, Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, United States
‡ Marine Science Institute, University of the Philippines, Diliman, Quezon City 1101, Philippines
§ Academy of Natural Sciences, 1900 Benjamin Franklin Parkway, Philadelphia, Pennsylvania 19103, United States
Department of Environmental and Biomolecular Systems, OGI School of Science & Engineering, Oregon Health & Science University, Beaverton, Oregon 97006, United States
Department of Biology, University of Utah, Salt Lake City, Utah 84112, United States
Department of Anesthesiology, University of Utah, Salt Lake City, Utah 84112, United States
J. Nat. Prod., Article ASAP
DOI: 10.1021/np200886x

Two new compounds, the peptide–polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey’s method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

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