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Note | Regular issue | Vol 57, No. 4, 2002, pp.697-704
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9369
Chemical Oxidation of Synthetic Iron(III)-Complex of 15-Phenyl Protoporphyrin IX

Fernando Niemevz, Diego E. Alvarez, and Graciela Y. Buldain*

*Cátedra de Química Orgánica II, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 3er. piso. (1113) Buenos Aires, Argentina

Abstract

Oxidative cleavage of 15-phenyl protohemin IX in pyridine solution in the presence of ascorbic acid (coupled oxidation), followed by esterification of the products with boron trifluoride-methanol rendered only three isomeric biliverdins. These were identified by 1H NMR and MS spectrometry as 10-phenyl biliverdin IXα (1), 5-phenyl biliverdin IXβ (2) and 15-phenyl biliverdin IXδ (3) dimethyl esters. The fact that biliverdin IXγ dimethyl ester derivative is not obtained indicates that oxidation fails to occur in the γ-meso-carbon bearing the phenyl group.