Metabolism of Tryptophan by Pseudomonas aureofaciens
| Autor: | R. L. Hamill, Marvin Gorman, James A. Mabe, Richard P. Elander |
|---|---|
| Rok vydání: | 1970 |
| Předmět: |
Indole test
Trifluoromethyl General Immunology and Microbiology biology Chemistry Stereochemistry Pseudomonas Tryptophan Substituent General Medicine biology.organism_classification General Biochemistry Genetics and Molecular Biology Pyrrolnitrin chemistry.chemical_compound Pseudomonas aureofaciens Biosynthesis General Pharmacology Toxicology and Pharmaceutics |
| Zdroj: | Applied Microbiology. 19:721-725 |
| ISSN: | 0003-6919 |
| DOI: | 10.1128/am.19.5.721-725.1970 |
| Popis: | Exogenous tryptophan is metabolized by Pseudomonas aureofaciens to yield pyrrolnitrin [3-chloro-4-(2′-nitro-3′-chlorophenyl)-pyrrole], an antifungal agent. The ability of this culture to metabolize tryptophan analogues in a similar manner was investigated by addition of the appropriate compound to the fermentation. Tryptophan precursors and metabolites or nonphenyl-substituted tryptophans had little effect on pyrrolnitrin biosynthesis, but simple derivatives of indole inhibited the production of pyrrolnitrin. Tryptophans substituted at the 4 position decreased pyrrolnitrin production and were converted into the corresponding substituted indoles. Tryptophans substituted at the 5, 6, and 7 position with fluorine or at the 5 and 7 position with methyl yielded new pyrrolnitrin derivatives. Substitution of larger groups (such as chloro, bromo, trifluoromethyl, and methoxy) at these positions led to the formation of the intermediate, amino pyrrolnitrin [3-chloro-4-(2′-amino-3′-chlorophenyl)-pyrrole], with the appropriate new substituent. The trifluoromethyl group at the 6 position of tryptophan prevented chlorination at the 3 position of pyrrolnitrin. |
| Databáze: | OpenAIRE |
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