U.S.-Korea Cooperative Research: Reduction of NAD+ Analoguesby Phosphonate

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This proposal requests funds to permit Dr. Maurice M. Kreevoy, Department of Chemistry, University of Minnesota, to pursue with Dr. In-Sook Han Lee, Department of Chemistry, Science Education Research Institute, Kangweon National University, for a period of 24 + months, a program of cooperative research on the reduction of NAD analogues (nicotinamide quarternary salts), including pyridinium, quinolinium, acridinium, and phenanthridinium halides, by mono- or disodium phosphonate. The nature of this reduction will be explored by characterizing the products by instrumental techniques and by determining the mechanism of the reaction by kinetic methods. The reduction of nicotinamide quarternary salts and their analogs has been a long standing objective because of the great importance of this process in biological systems and the possible use of nicotinamide enzymes in synthetic transformation. Although many of these reactions could be valuable in practical organic synthesis, enzyme-catalyzed oxidation-reduction reactions of this type have not been very successful because the reduced cofactors are expensive to produce, some are not commercially available, some are unstable in solution, and others leave undesirable by-products. Phosphonate used as a reducing agent has several advantages, namely, it is a strong enough reducing + agent to produce a wide range of reactions with a variety of NAD analogs and it is inexpensive, commercially available, stable in solution, and its end product is not likely to produce side reactions. This project is relevant to the objectives of the U.S.-Korea Cooperative Science Program which seeks to increase the level of cooperation between U.S. and Korean scientists and engineers through the exchange of scientific information, ideas, skills, and techniques and through collaboration on problems of mutual benefit. This project will add an international cooperative dimension to Dr. Kreevoy's research under NSF Grant No. CHE-8520903.