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 journalArticle

19 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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    Lin, Z., Flores, M., Forteza, I., Henriksen, N. M., Concepcion, G. P., Rosenberg, G., Haygood, M. G., Olivera, B. M., Light, A. R., Cheatham, T. E., & Schmidt, E. W. (2012). Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp. Journal of Natural Products, 75(4), 644-649. https://doi.org/10.1021/np200886x