ORGN 306 |
Rearrangement of 5-hydroxy-8-oxoguanosine, a guanosine oxidation intermediate
| Jeremy McCallum, Department of Chemistry and Biochemistry, UCLA, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA 90095 and Christopher S. Foote, Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA CA90095. |
Oxidation of 8-oxoguanosine with singlet oxygen yielded 5,8-dihydro-5-hydroperoxy-8-oxoguanosine. Reduction of this intermediate at low temperature afforded the corresponding alcohol, the long-postulated 5,8-dihydro-5-hydroxy-8-oxoguanosine (1). Upon warming to room temperature, this alcohol rearranges to form spiroiminodihydantoin (2) in good yield within two hours. At low pH, a different product is formed. |
| |
|
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
|