Intermediates in the oxidation of 8-oxoguanosine: Reactions of 5-hydroperoxy-8-oxoguanosine

ORGN 292

Corrie Y. Kuniyoshi and Christopher S. Foote. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095
Low-temperature NMR studies have shown that 5-hydroperoxy-8-oxoguanosine (1) is a key intermediate in the type II photosensitized oxidation of 8-oxoguanosine. Compound 1 can be reduced by treatment with dimethylsulfide to form 5-hydroxy-8-oxoguanosine 2 and dimethylsulfoxide. The monooxygen transfer ability of 1 has been probed by kinetic studies comparing 1 to other hydroperoxides, and the relative reactivities have been further explained using density functional theory calculations.

 

Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004