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

ORGN 140

Fu-Lian Hsu, fulian.hsu@us.army.mil1, Mark D. Winemiller1, Frederic J. Berg1, Vipin K. Rastogi2, and Tu-chen Cheng2. (1) Department of Physical and Chemical Sciences, US Army Edgewood Chemical Biological Center, Ricketts Point Road, Aberdeen Proving Ground, MD 21010-5424, (2) Department of Toxicology, US Army Edgewood Chemical Biological Center, Ricketts Point Road, 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 shown to be stable and can be stored for many years. However, a simple method validating the continued efficacy of the enzyme 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.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005