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Appl Environ Microbiol. 1970 May; 19(5): 721-725
Copyright © 1970 American Society for Microbiology. All Rights Reserved.

Metabolism of Tryptophan by Pseudomonas aureofaciens

III. Production of Substituted Pyrrolnitrins from Tryptophan Analogues ¹

Fermentation Products Research Division, The Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46206

ABSTRACT

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.

² Present address: Wyeth Laboratories, Inc., West Chester, Pa. 19380.

¹ Part of this study was reported at the 154th meeting of the American Chemical Society, Chicago, Ill., September 1967.