Heteroaromatic monothiocarboxylic acids from Pseudomonas spp.
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- Budzikiewicz, H. Biodegradation (2003) 14: 65. doi:10.1023/A:1024012015127
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Pyridine derivatives substituted with monothiocarboxylic acid groups are the uniquemetabolites of certain Pseudomonas species. Pyridine-2,6-di-(monothiocarboxylic acid) 1a was found during a screening program for antibiotically active bacterial metabolites due to its ability to complex Fe3+. The structure of this complex, itsredox behavior and the biogenesis of the ligand molecule were studied in detail. Thislead to the discovery of a new class of natural products, viz. acylsulfenic acid derivatives. Interest in 1a was revived shortly when complexes with other metals were studied as models for sulfur-containing enzymes. It could also be shown that a quinoline monothiocarboxylic acid derivative acted as an alternative siderophorefor Pseudomonas fluorescens. But a real renaissance was observed only whenthe role of 1a in the degradation of CCl4 by Pseudomonas stutzeri became evident.