Heteroaromatic monothiocarboxylic acids from Pseudomonas spp.
Pyridine derivatives substituted with monothiocarboxylic acid groups are the unique metabolites 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, its redox behavior and the biogenesis of the ligand molecule were studied in detail. This lead to the discovery of a new class of natural products, viz. acylsulfenic acid derivatives. Interest in la 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 siderophore for Pseudomonas fluorescens. But a real renaissance was observed only when the role of la in the degradation of CCl4 by Pseudomonas stutzeri became evident.
Budzikiewicz
H
H
Institut für Organische Chemie, Universität zu Köln, D-50939 Köln, Germany. aco88@uni-koeln.de
D001673:Biodegradation, Environmental; D002264:Carboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry* / Q000302:isolation & purification; D007501:Iron / Q000378:metabolism; D010084:Oxidation-Reduction; D011549:Pseudomonas / Q000737:chemistry / Q000378:metabolism*; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification; D011804:Quinolines; D017262:Siderophores / Q000737:chemistry / Q000302:isolation & purification; D012988:Soil Microbiology
D002264:Carboxylic Acids; D006573:Heterocyclic Compounds, 1-Ring; D011725:Pyridines; D011804:Quinolines; D017262:Siderophores; C404845:quinolobactin; D007501:Iron