Metabolism of Tryptophan by Pseudomonas aureofaciens: III. Production of Substituted Pyrrolnitrins from Tryptophan Analogues 1
AUTOR(ES)
Hamill, R. L.
RESUMO
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.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=376776Documentos Relacionados
- Metabolism of Tryptophans by Pseudomonas aureofaciens: VI. Production of Pyrrolnitrin by Selected Pseudomonas Species
- METABOLISM OF CARBOHYDRATES BY PSEUDOMONAS SACCHAROPHILA III. : Oxidation of d-Arabinose1
- Chorismate Mutase from Streptomyces aureofaciens: a Heat-Stable Enzyme
- Metabolism of Pyrimidine Nucleotides in a Microorganism: III. Enzymatic Production of Ribose-5-Phosphate from Uridine-5′-Monophosphate by Pseudomonas oleovorans
- Metabolism of Biotin and Analogues of Biotin by Microorganisms III. Degradation of Oxybiotin and Desthiobiotin by Lactobacillus plantarum