HETEROCYCLES

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■ On the Formation of Bile Pigments from Heme Proteins

Andrew D. Hamilton and David Dolphin*

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada

Abstract

It is proposed that the catabolism of heme to biliverdin involves a initial epoxidation of a protein-bound porphyrin at the exposed γ-methine bridge. Rearrangement of the γ- to an α-epoxide follwed by ring opening to a homooxaporphyrin would generate an electron-rich system capable of reacting with molecular oxygen to form a dioxetane. Fragmentation of the dioxetane to a mono formate ester of biliverdin followed by loss of carbon monoxide would give the bile pigment.