An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B
| Autor: | Rou-Jie Huang, Dehai Li, Ranuka T. Hewage, Yu-Ju Chen, Shao-Hsing Weng, Ya-Chu Lien, Shu-Jung Lai, Hsiao-Ching Lin, Rong-Jie Chein, Shih-Hsiung Wu |
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| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Natural product Molecular Structure ATP synthase biology Stereochemistry Organic Chemistry Imidazoles Ovomucin medicine.disease_cause Biochemistry chemistry.chemical_compound Enzyme chemistry Biosynthesis Staphylococcus aureus Michael reaction medicine biology.protein Imidazole Diterpenes Physical and Theoretical Chemistry Diterpene |
| Zdroj: | Organic Letters. 23:1904-1909 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c00330 |
| Popis: | Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B (1), which involves a diterpene synthase and a P450 monooxygenase. In addition, an α,β-hydrolase (Con-ABH) was shown to catalyze an aza-Michael addition between 1 and imidazole to give 3S-imidazolyl conidiogenone B (6). Compound 6 was more potent than 1 against Staphylococcus aureus strains. |
| Databáze: | OpenAIRE |
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