ORGN 769 |
| Our project aims to develop new and improved methods for the detection of highly toxic organophosphonates. The organophosphonates and phosphates such as tabun, sarin and soman, are among the most toxic chemical warfare agents known. These agents are powerful inhibitors of acetylcholinesterase, which is critical in nerve function. Diisopropylfluorophosphate (DFP) and diethylchlorophosphate (DCP) have similar reactivity, and hence they can be the good model compounds for the design of indicators. We plan to develop sensitive, fluorescent chemosensors for the detection of nerve agents. These toxins block nerve function by reacting with a hydroxyl group at the catalytic site of acetylcholinesterase, forming a phosphate and phosphonate ester. Our proposed chemosensor, the quinolin-2-one derivative, is designed to utilize this reactivity toward nucleophiles. The initial adduct is expected to undergo an intramolecular cyclization reaction to form the resonance stabilized cation. The expected fluorescence of desired product will be used to detect and quantify the nerve agent. The planned synthesis of our chemosensor involves nine steps, starting from m-nitroaniline. Several synthetic steps have been completed and our current progress will be described.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |