Cyclodextrin aldehydes are oxidase mimics.
Cyclodextrins containing 6-aldehyde groups were found to catalyse oxidation of aminophenols in the presence of hydrogen peroxide. The catalysis followed Michaelis-Menten kinetics and is related to the catalysis previously observed with cyclodextrin ketones. A range of different cyclodextrin aldehydes were prepared containing one, two or more aldehydes at the primary rim (6-positions) or a ethoxy-2-al or propoxy-3-al at the secondary rim. 2-O-ethoxy-2-al-beta-cyclodextrin (22) was found to be the best catalyst. The aldehydes are in many cases better catalysts than the ketones, because of their powerful covalent binding of hydrogen peroxide.
Hauch Fenger
Thomas
T
Department of Chemistry and Nanoscience Center, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen.
Bjerre
Jeannette
J
Bols
Mikael
M
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000627:Aminophenols / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003505:Cyclodextrins / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D007700:Kinetics; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism*; D011803:Quinine / Q000737:chemistry
D000447:Aldehydes; D000627:Aminophenols; D003505:Cyclodextrins; D007097:Imines; D011803:Quinine; D010088:Oxidoreductases