Abstract
Photo-oxidation of bilirubin in methanol containing anhydrous ammonia (0·2%) rapidly destroys the substrate. Methylvinylmaleimide, three methanol–propentdyopent adducts, and a water–propentdyopent adduct have been isolated. Arguments are presented which allow structures to be assigned to the propentdyopent adducts, and the absence of a fourth methanol–propentdyopent isomer is rationalised. Equilibration between a pair of unsymmetrically substituted methanol–propentdyopent adducts occurs on irradiation (of the free acids), on treatment with zinc acetate, and on treatment with 10% acetic acid in chloroform. A dipyrrylmethane dialdehyde obtained from an aqueous photolysate of bilirubin has been characterised. Mechanistic aspects of the photo-oxidation are discussed.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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