Novel catecholate-type siderophore analogs based on a myo-inositol scaffold.
A novel 1,3,5-triamino-myo-inositol derivative is presented as a readily available scaffold for the design of tripodal siderophore mimetics. Based on this scaffold, various hexadentate catecholate-type siderophore analogs were synthesized by attaching the catechols to the inositol scaffold via spacer units of different structure and length. The potential to tune the polarity of the inositol containing siderophore analogs has also been demonstrated by varying the protection group strategy. The siderophore activity of the prepared siderophore analogs was examined by cross-feeding tests with various Gram-negative bacteria and mycobacteria.
Schnabelrauch
M
M
Hans Knöll-Institut für Naturstoff-Forschung, Jena, Germany.
Egbe
D A
DA
Heinisch
L
L
Reissbrodt
R
R
Möllmann
U
U
D002396:Catechols / Q000737:chemistry*; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000378:metabolism; D007294:Inositol / Q000737:chemistry; D009161:Mycobacterium / Q000378:metabolism; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry*
D002396:Catechols; D002614:Chelating Agents; D017262:Siderophores; D007294:Inositol