Structure and absolute stereochemistry of the four N-phenylprotoporphyrin IX regioisomers isolated from phenylhydrazine-treated myoglobin

The phenyl-iron complex formed in the reaction of phenylhydrazine with equine myoglobin rearranges, in the presence of acid and oxygen, to a mixture of the four possible N-phenylprotoporphyrin IX regioisomers. The four isomers have been separated, and the pyrrole ring bearing the N-phenyl group in e...

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Veröffentlicht in:Journal of the American Chemical Society 1991-10, Vol.113 (21), p.8146-8153
Hauptverfasser: Swanson, Barbara A, Ortiz de Montellano, Paul R
Format: Artikel
Sprache:eng
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Zusammenfassung:The phenyl-iron complex formed in the reaction of phenylhydrazine with equine myoglobin rearranges, in the presence of acid and oxygen, to a mixture of the four possible N-phenylprotoporphyrin IX regioisomers. The four isomers have been separated, and the pyrrole ring bearing the N-phenyl group in each of them has been identified by super(1)H NMR spectroscopy. The isomers are chiral, an their circular dichroism spectra have been determined.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00021a046