3-Indolyl methylphosphonate and methylphosphonothioate as indicators for enzyme-based decontamination of organophosphonoate agents

ORGN 105

Mark D. Winemiller, Fu-Lian Hsu, Fred Berg, Tu chen Cheng, and Vipin K. Rastogi. U.S. Army Edgewood Chemical Biological Center, Aberdeen Proving Ground, MD 21010-5424

Hydrolysis and oxidation are commonly used chemical reactions for the decontamination of toxic organophosphonate compounds. Enzymatic hydrolysis of organophosphonates by organophosphorus acid hydrolase (OPH) and organophosphorus acid anhydrolase (OPAA) has been demonstrated to be effective under mild conditions. The freeze-dried OPH and OPAA prepared with trehalose are stable and can be stored for many years. However, a simple method validating the contiuned efficacy of the enzymes is necessary. This paper describes the synthesis of the title compounds from the corresponding phosphonocyanidate and 3-hydroxyindole or 3-mercaptoindole. The reaction of the title compounds with OPH and OPAA demonstrates a simple yet effective method for the monitoring of OPH and OPAA efficacy.

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics 8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004