Metabolic products of microorganisms

✍ Scribed by J. Ernst; G. Winkelmann

• Publisher: Springer
• Year: 1974
• Tongue: English
• Weight: 586 KB
• Volume: 100
• Category: Article
• ISSN: 0302-8933
• DOI: 10.1007/bf00446323

✦ Synopsis

Different derivatives of coprogen B (desacetyl coprogen) and eoprogen 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 OR-groups of the anhydromevalonic moieties, like di-O-acetylation and di-O-suceinylation 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 Neuro~'pora crassa. The results suggest that the coprogen molecule requires a special hydrophobic area for optimal orientation during uptake and iron release.