Alpha-keto acids are novel siderophores in the genera Proteus, Providencia, and Morganella and are produced by amino acid deaminases.
Growth promotion and iron transport studies revealed that certain alpha-keto acids generated by amino acid deaminases, by enterobacteria of the Proteus-Providencia-Morganella group (of the tribe Proteeae), show significant siderophore activity. Their iron-binding properties were confirmed by the chrome azurol S assay and UV spectra. These compounds form ligand-to-metal charge transfer bands in the range of 400 to 500 nm. Additional absorption bands of the enolized ligands at 500 to 700 nm are responsible for color formation. Siderophore activity was most pronounced with alpha-keto acids possessing an aromatic or heteroaromatic side chain, like phenylpyruvic acid and indolylpyruvic acid, resulting from deamination of phenylalanine and tryptophan, respectively. In addition, alpha-keto acids possessing longer nonpolar side chains, like alpha-ketoisocaproic acid or alpha-ketoisovaleric acid and even alpha-ketoadipic acid, also showed siderophore activity which was absent or negligible with smaller alpha-keto acids or those possessing polar functional groups, like pyruvic acid, alpha-ketobutyric acid, or alpha-ketoglutaric acid. The fact that deaminase-negative enterobacteria, like Escherichia coli and Salmonella spp., could not utilize alpha-keto acids supports the view that specific iron-carboxylate transport systems have evolved in members of the tribe Proteeae and are designed to recognize ferric complexes of both alpha-hydroxy acids and alpha-keto acids, of which the latter can easily be generated by L-amino acid deaminases in an amino acid-rich medium. Exogenous siderophores, like ferric hydroxamates (ferrichromes) and ferric polycarboxylates (rhizoferrin and citrate), were also utilized by members of the tribe Proteeae.
Drechsel
H
H
Institut für Organische Chemie, Universität Tübingen, Germany.
Thieken
A
A
Reissbrodt
R
R
Jung
G
G
Winkelmann
G
G
D000596:Amino Acids / Q000378:metabolism*; D001681:Biological Assay; D001692:Biological Transport; D002208:Caproates / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003641:Deamination; D004755:Enterobacteriaceae / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism*; D006877:Hydroxamic Acids / Q000378:metabolism; D007501:Iron / Q000378:metabolism*; D007651:Keto Acids / Q000378:metabolism* / Q000494:pharmacology; D007773:Lactates / Q000378:metabolism; D007930:Leucine / Q000378:metabolism; D010649:Phenylalanine / Q000378:metabolism; D010667:Phenylpyruvic Acids / Q000378:metabolism; D011511:Proteus / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism; D011532:Providencia / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism; D017262:Siderophores / Q000378:metabolism* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014364:Tryptophan / Q000378:metabolism; D014633:Valine / Q000378:metabolism
D000596:Amino Acids; D002208:Caproates; D006877:Hydroxamic Acids; D007651:Keto Acids; D007773:Lactates; D010667:Phenylpyruvic Acids; D017262:Siderophores; C017648:3-phenyllactic acid; D010649:Phenylalanine; C019419:alpha-hydroxyisocaproic acid; C013082:alpha-ketoisocaproic acid; D014364:Tryptophan; D007501:Iron; D007930:Leucine; D014633:Valine; C031606:phenylpyruvic acid