Metabolism of tryptophan by Pseudomonas aureofaciens. 3. Production of substituted pyrrolnitrins from tryptophan analogues.
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.
D000935:Antifungal Agents / Q000096:biosynthesis* / Q000302:isolation & purification; D001681:Biological Assay; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D005285:Fermentation; D005782:Gels; D006219:Halogens / Q000378:metabolism; D007211:Indoles / Q000378:metabolism; D007259:Infrared Rays; D009682:Magnetic Resonance Spectroscopy; D009491:Neurospora; D011549:Pseudomonas / Q000378:metabolism*; D011758:Pyrroles / Q000096:biosynthesis* / Q000302:isolation & purification; D012822:Silicon Dioxide; D013057:Spectrum Analysis; D014364:Tryptophan / Q000378:metabolism*; D014466:Ultraviolet Rays
D000935:Antifungal Agents; D005782:Gels; D006219:Halogens; D007211:Indoles; D011758:Pyrroles; D012822:Silicon Dioxide; D014364:Tryptophan