Abstract
Different derivatives of coprogen B (desacetyl coprogen) and coprogen were prepared to study their iron transport properties in Neurospora crassa arg-5, ota, aga. With increasing N-acyl chain length the rates of iron chelate uptake could significantly be enhanced in the order N-acetyl-<N-propionyl-<N-butyryl coprogen B. However, more bulky phenyl derivatives and lipophilic, charge carrying N-acyl derivatives again decreased the uptake rates, although their affinity to the uptake system is increased. On the other hand, structural alterations of the two OH-groups of the anhydromevalonic moieties, like di-O-acetylation and di-O-sucinylation revealed no improvement of the chelate uptake. Di-O-acetyl coprogen showed similar transport properties like coprogen, whereas di-O-succinyl coprogen exhibited a remarkably lower affinity to the coprogen uptake system in Neurospora crassa. The results suggest that the coprogen molecule requires a special hydrophobic area for optimal orientation during uptake and iron release.
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Ernst, J., Winkelmann, G. Metabolic products of microorganisms. Arch. Microbiol. 100, 271–282 (1974). https://doi.org/10.1007/BF00446323
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DOI: https://doi.org/10.1007/BF00446323