Tailoring mimics of sugar-transforming enzymes: Regioselective alcohol oxidation

CARB 75

Susanne Striegler, susanne.striegler@auburn.edu, Department of Chemistry & Biochemistry, Auburn University, 179 Chemistry Building, Auburn, AL 36849
Galactose oxidase transforms carbohydrates with 'galacto' configuration into the corresponding aldehydes. The high stereoselectivity of this reaction renders the enzyme extremely attractive for the preparation of unnatural carbohydrates, relevant for the design of new pharmaceuticals. From a practical point of view, however, recognition of carbohydrates with 'galacto' configuration only, low thermostability, and a narrow pH range limit the potential of the enzyme for broad application. Transition metal catalysts, on contrast, exhibit high catalytic turnover with good thermostability, but lack the requisite capabilities to selectively transform one particular carbohydrate in mixtures. The objective of our research is to combine enzyme-like selectivity with the practicality of transition metal catalysts in new designed materials. Towards this end, selective differentiation of carbohydrates by a dinuclear metal complex was reported. Preliminary results further show oxidation ability for the same complex. Current efforts towards the development of new carbohydrate transforming enzyme mimics will be discussed.