Studies on the Biosynthesis of the Notoamides: Synthesis of an Isotopomer of 6-Hydroxydeoxybrevianamide E and Biosynthetic Incorporation into Notoamide J
- 19 April 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (15), 5954-5958
- https://doi.org/10.1021/jo200218a
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, [13C]2-[15N]-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.Keywords
This publication has 18 references indexed in Scilit:
- Notoamide E: biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600Tetrahedron Letters, 2011
- Genome-Based Characterization of Two Prenylation Steps in the Assembly of the Stephacidin and Notoamide Anticancer Agents in a Marine-Derived Aspergillus sp.Journal of the American Chemical Society, 2010
- Notoamide O, a Structurally Unprecedented Prenylated Indole Alkaloid, and Notoamides P−R from a Marine-Derived Fungus, Aspergillus sp.Journal of Natural Products, 2010
- Synthesis of Notoamide J: A Potentially Pivotal Intermediate in the Biosynthesis of Several Prenylated Indole AlkaloidsThe Journal of Organic Chemistry, 2010
- Asymmetric total syntheses of (+)- and (−)-versicolamide B and biosynthetic implicationsNature Chemistry, 2009
- Isolation of Notoamide E, a Key Precursor in the Biosynthesis of Prenylated Indole Alkaloids in a Marine-Derived Fungus, Aspergillus sp.Journal of the American Chemical Society, 2009
- Isolation of Antipodal (−)-Versicolamide B and Notoamides L−N from a Marine-Derived Aspergillus sp.Organic Letters, 2009
- Notoamides F−K, Prenylated Indole Alkaloids Isolated from a Marine-Derived Aspergillus sp.Journal of Natural Products, 2008
- Premalbrancheamide: Synthesis, Isotopic Labeling, Biosynthetic Incorporation, and Detection in Cultures of Malbranchea aurantiacaOrganic Letters, 2008
- Isolation, Structure Elucidation, and Biomimetic Total Synthesis of Versicolamide B, and the Isolation of Antipodal (−)‐Stephacidin A and (+)‐Notoamide B from Aspergillus versicolor NRRL 35600Angewandte Chemie-International Edition, 2008