ARTIFICIAL REDOX ENZYMES .1. SYNTHETIC STRATEGIES

Organic models of flavoenzymes consist of a binding site covalently attached to a flavin derivative acting as the catalytic site. The earlier reported synthesis of such a model using alpha-cyclodextrin as the binding site proved to be difficult to reproduce with beta-cyclodextrin. The synthetic strategy involved attaching a fully constructed riboflavin onto a cyclodextrin by a nucleophilic reaction. Riboflavin was found to decompose under the reaction conditions. A new method for the synthesis of flavocyclodextrins involving construction of the flavin moiety onto cyclodextrin is convenient and can be used to synthesize 6-flavocyclodextrins and 2-flavocyclodextrins.