title: Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.
abstract: 6-Hydroxydeoxybrevianamide E is proposed as a biosynthetic precursor to several advanced metabolites isolated from both marine-derived Aspergillus sp. and a terrestrial-derived Aspergillus versicolor. To verify the role of this reverse-prenylated indole alkaloid as an intermediate along the biosynthetic pathway, [(13)C](2)-[(15)N]-6-hydroxydeoxybrevianamide E was synthesized and fed to Aspergillus versicolor. Analysis of the metabolites showed incorporation of the intermediate only into the natural product notoamide J.
authors.affiliation: Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, Colorado 80523, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Finefield
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D001230:Aspergillus / Q000737:chemistry* / Q000378:metabolism; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054876:Prenylation
chemical_list: C569086:6-hydroxydeoxybrevianamide E; D026121:Indole Alkaloids; C551124:notoamide J