Synthesis and Bioconversions of Notoamide T: A Biosynthetic Precursor to Stephacidin A and Notoamide B
| Autor: | Timothy J. McAfoos, Robert M. Williams, Jennifer M. Finefield, David H. Sherman, Hikaru Kato, Sachiko Tsukamoto, Shengying Li, James D. Sunderhaus |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Biological Products
Molecular Structure Stereochemistry Metabolite Organic Chemistry Total synthesis Stereoisomerism Stephacidin Notoamide B Biochemistry Article Indole Alkaloids chemistry.chemical_compound Aspergillus chemistry Aspergillus versicolor Physical and Theoretical Chemistry Notoamide T Biogenesis |
| Zdroj: | Organic Letters. 15:22-25 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol302901p |
| Popis: | In an effort to further elucidate the biogenesis of the stephacidin and notoamide families of natural products, notoamide T has been identified as the likely precursor to stephacidin A. The total synthesis of notoamide T is described along with it is C-6-epimer, 6-epi-notoamide T. The chemical conversion of stephacidin A to notoamide T by reductive ring opening is described as well as the oxidative conversion of notoamide T to stephacidin A. Furthermore, [(13)C](2)-notoamide T was synthesized and provided to Aspergillus versicolor and Aspergillus sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|