Synthesis of sulfur-substituted quinones from the oxidation of 5-methyl-4-mercapto-catechol and 5-methyl-3,4-dimercapto-catechol

TOXI 79

Adaickapillai Mahendran, agreer@brooklyn.cuny.edu1, David Aebisher, agreer@brooklyn.cuny.edu1, Alvaro Castillo, agreer@brooklyn.cuny.edu1, Joel F. Liebman, jliebman@umbc.edu2, and Alexander Greer, agreer@brooklyn.cuny.edu1. (1) Department of Chemistry and Graduate Center, City University of New York, Brooklyn College, 2900 Bedford Ave., Brooklyn, NY 11210, (2) Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250
Quinones derived from 6-mercaptodopamine (1) and 5,6-dimercaptodopamine (2) may serve as precursors for sulfur-containing natural products, such as thianthrenes and tetrathiocins extracted from marine invertebrates. Thus, we undertook an experimental effort to generate possible quinones from a model system, which used 4-mercapto-5-methyl catechol (3) and 3,4-dimercapto-5-methyl catechol (4) as reagents. The formation of quinones and dimers from the oxidation of 3 and 4 are assessed by NMR, HPLC, and mass spectrometry. The experimental data will also be compared with our DFT computations.

 

Poster Session and Awards
6:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- 204 A/B, Poster

Division of Chemical Toxicology

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007