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, Eric W. Schmidt

    Research output: Contribution to journalArticlepeer-review

    28 Scopus citations

    Abstract

    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.

    Original languageEnglish (US)
    Pages (from-to)644-649
    Number of pages6
    JournalJournal of Natural Products
    Volume75
    Issue number4
    DOIs
    StatePublished - Apr 27 2012

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Molecular Medicine
    • Pharmacology
    • Pharmaceutical Science
    • Drug Discovery
    • Complementary and alternative medicine
    • Organic Chemistry

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