Biosynthesis of the Immunosuppressant (-)-FR901483
| Autor: | Zhuan Zhang, Michio Sato, Masatoshi Taniguchi, Satoshi Sasamura, Tianzhang Qiao, Man-Cheng Tang, Yui Tamura, Yoshihiro Otsu, Kenji Watanabe, Yi Tang |
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| Rok vydání: | 2020 |
| Předmět: |
Annulation
Chemistry Stereochemistry Alkaloid Regioselectivity General Chemistry Biochemistry Catalysis Article Enzymes Fungal Proteins chemistry.chemical_compound Colloid and Surface Chemistry Organophosphorus Compounds Biosynthesis Ascomycota Multigene Family Phosphorylation Aldol condensation Stereoselectivity Heterologous expression Immunosuppressive Agents |
| Zdroj: | J Am Chem Soc |
| ISSN: | 1520-5126 |
| Popis: | We report characterization of the biosynthetic pathway of the potent immunosuppressant (-)-FR901483 (1) through heterologous expression and enzymatic assays. The biosynthetic logic to form the azatricyclic alkaloid is consistent with those proposed in biomimetic syntheses and involves aza-spiro annulation of dityrosyl-piperazine to form a ketoaldehyde intermediate, followed by regioselective aldol condensation, stereoselective ketoreduction, and phosphorylation. A possible target of 1 is proposed based on the biosynthetic studies. |
| Databáze: | OpenAIRE |
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