New synthetic catecholate-type siderophores based on amino acids and dipeptides.
New analogs of bacterial siderophores with one, two or three catecholate moieties were synthesized using various mono- and diamino acid and dipetide scaffolds, respectively. In addition to 2,3-dihydroxybenzoyl siderophore analogs and their acylated derivatives, 3,4-dihydroxybenzoyl derivatives were prepared. Furthermore, the synthesis of a new triscatecholate serving as an intimate model for enterobactin is reported. Most of the new compounds gave a positive CAS-test and were active as siderophores tested by growth promotion assays with a set of siderophore indicator mutants under iron limitation. Structure-activity-correlations have also been studied.
Schnabelrauch
M
M
Hans Knöll-Institut for Natural Product Research, Jena, Germany.
Wittmann
S
S
Rahn
K
K
Möllmann
U
U
Reissbrodt
R
R
Heinisch
L
L
D000596:Amino Acids / Q000737:chemistry; D002396:Catechols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004151:Dipeptides / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000235:genetics / Q000254:growth & development; D009154:Mutation; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000596:Amino Acids; D002396:Catechols; D004151:Dipeptides; D017262:Siderophores