β-Cyclodextrin–nicotinamide as a model for NADH dependent enzymes

Abstract

The newly synthesized β-cyclodextrin–nicotinamides (1) and (2) have a nicotinamide group on the secondary hydroxy-side of β-cyclodextrin, in an axial configuration for (1) and equatorial for (2). The corresponding reduced forms (3) and (4) can reduce ninhydrin with large rate enhancements (40- and 60-fold, respectively) relative to NADH. They also show enzyme-like saturation kinetics in the reduction of ninhydrin, which indicates that the reaction involves complex formation.