title: Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.
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.
authors.affiliation: College of Pharmacy, Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
authors.forename: Zhenjian
authors.initials: Z
authors.lastname: Lin
authors.forename: Malem
authors.initials: M
authors.lastname: Flores
authors.forename: Imelda
authors.initials: I
authors.lastname: Forteza
authors.forename: Niel M
authors.initials: NM
authors.lastname: Henriksen
authors.forename: Gisela P
authors.initials: GP
authors.lastname: Concepcion
authors.forename: Gary
authors.initials: G
authors.lastname: Rosenberg
authors.forename: Margo G
authors.initials: MG
authors.lastname: Haygood
authors.forename: Baldomero M
authors.initials: BM
authors.lastname: Olivera
authors.forename: Alan R
authors.initials: AR
authors.lastname: Light
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Cheatham
authors.forename: Eric W
authors.initials: EW
authors.lastname: Schmidt
mesh_terms: D000818:Animals; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D008974:Mollusca / Q000382:microbiology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D010679:Philippines; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification*; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D006027:Glycosides; D010456:Peptides, Cyclic; D061065:Polyketides; C573064:totopotensamide A; C573065:totopotensamide B