ORGN 241 |
Advances in rhodoquinone biosynthesis
| Jennifer N. Shepherd1, Jeffrey Strahan1, and Thomas Varner2. (1) Department of Chemistry, Gonzaga University, 502 E. Boone Avenue, Spokane, WA 99258-0005, (2) Science Department, Wellpinit School, P.O. Box 390, Wellpinit, WA 99040 |
Rhodoquinone (RQ) is an aminoquinone which serves as an important electron carrier in anaerobic energy metabolism. Species such as the helminth parasites, Caenorhabditis elegans and Rhodospirillaceae bacteria depend on RQ for survival under anaerobic conditions. Selective inhibition of RQ biosynthesis may lead to highly specific anthelminthic and antibacterial agents since host organisms do not produce or require RQ for energy production. The structure of RQ closely resembles ubiquinone (Q), of which the biosynthesis has been well-documented. The focus of this research was to identify the immediate biosynthetic precursor to RQ. We investigated three proposed precursors to RQ (demethoxyQ-3, demethylQ-3 and Q-3). Rhodospirillum rubrum bacteria were fed each of the proposed precursors at 10 micromolar concentration. The formation of Q-3 and RQ-3 were observed after feeding demethylQ-3 to R. rubrum by HPLC analysis. The identity of RQ-3 has yet to be verified by MS. DemethoxyQ-3 and Q-3 did not produce RQ-3.  |
| |
|
Lipids, Biosynthesis, Enzyme Inhibitors, and Mimetics
8:00 AM-11:20 AM, Tuesday, March 30, 2004 Anaheim Convention Center -- 303D, Oral
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
|