The biosynthesis of brominated pyrrolnitrin derivatives by Pseudomonas aureofaciens.
The mutant strain ACN of Pseudomonas aureofaciens ATCC 15926 produces several bromo derivatives of pyrrolnitrin. Five brominated amino- and three brominated nitrophenyl pyrrole compounds could be isolated, and their structures were established by 1H NMR, UV and mass spectroscopy. The isolated amino compounds showed no biological activity; the nitro derivatives inhibited the growth of Neurospora crassa ATCC 9276, though not as effective as pyrrolnitrin itself. 2-Carboxy-4-(2-amino-3-bromophenyl)pyrrole (X) is demonstrated to be an intermediate in the biosynthesis of brominated pyrrolnitrin; the biosynthetic pathway to bromo derivatives of pyrrolnitrin is discussed.
D000935:Antifungal Agents / Q000096:biosynthesis*; D002851:Chromatography, High Pressure Liquid; D013058:Mass Spectrometry; D011549:Pseudomonas / Q000378:metabolism*; D011764:Pyrrolnitrin / Q000096:biosynthesis*; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D011764:Pyrrolnitrin