A ThDP-dependent enzymatic carboligation reaction involved in Neocarazostatin A tricyclic carbazole formation
| Autor: | Li Su, Yi Yu, Zixin Deng, Hai Deng, Meinan Lv, Kwaku Kyeremeh |
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| Rok vydání: | 2016 |
| Předmět: |
Indoles
Stereochemistry Kinetics Carbazoles 010402 general chemistry 01 natural sciences Biochemistry Coupling reaction Enzyme catalysis chemistry.chemical_compound Pyruvic Acid Physical and Theoretical Chemistry Phylogeny chemistry.chemical_classification 010405 organic chemistry Carbazole Organic Chemistry Streptomyces Biosynthetic Pathways 0104 chemical sciences Enzyme chemistry Genes Bacterial Multigene Family Thiamine Thiamine Pyrophosphate Tricyclic |
| Zdroj: | Organic & Biomolecular Chemistry. 14:8679-8684 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c6ob01651k |
| Popis: | Although the biosynthetic pathway of Neocarazostatin A (1) has been identified, the detailed enzymatic reactions underlying the assembly of the carbazole ring still remain largely unknown. We demonstrate here that NzsH, a putative thiamine diphosphate dependent enzyme, can catalyze an acyloin coupling reaction between indole-3-pyruvate and pyruvate to generate a β-ketoacid intermediate. Our findings thus shed light on further characterization of the unusual biosynthetic pathway of the bacterial tricyclic carbazole alkaloids. |
| Databáze: | OpenAIRE |
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