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Stoffwechselprodukte von Mikroorganismen. 174. Mitteilung Eine neue Synthese des Ferrichroms; enantio-Ferrichrom

✍ Scribed by Hans-Ulrich Naegeli; Walter Keller-Schierlein

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
491 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Metabolites of Microorganisms. A New Synthesis of Ferrichrome; enantio‐Ferrichrome

The enantiomer of the natural sideramine ferrichrome was synthesized starting from D‐ornithine. The cyclohexapeptide (D‐Orn)~3~‐Gly~3~ was obtained by conventional methods of polypeptide chemistry. For the oxidation of the δ‐amino groups of the D‐ornithine residues to hydroxylamino groups the oxaziridine pathway was successful. The final steps ‐ introduction of the acetyl groups and formation of the iron trihydroxamate complex ‐ followed known procedures. The spectroscopic and chromatographic properties of the crystalline product corresponded to those of natural ferrichrome, the optical rotations and CD. curves being opposite. The biological activity of enantio‐ferrichrome was similar to that of the natural sideramine.

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