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Stoffwechselprodukte von Mikroorganismen. 174. Mitteilung Eine neue Synthese des Ferrichroms; enantio‐Ferrichrom
Author(s) -
Naegeli HansUlrich,
KellerSchierlein Walter
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610615
Subject(s) - chemistry , ferrichrome , stereochemistry , enantiomer , oxaziridine , natural product , biochemistry , escherichia coli , bacterial outer membrane , gene
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.