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Kinetic assessment of N-methyl-2-methoxypyridinium species as phosphonate anion methylating agents.

ABSTRACT: Organophosphate nerve agents and pesticides are potent inhibitors of acetylcholinesterase (AChE). Although oxime nucleophiles can reactivate the AChE-phosphyl adduct, the adduct undergoes a reaction called aging. No compounds have been described that reactivate the aged-AChE adduct. A family of 2-methoxypyridinium species which reverse aging in a model system is presented. A kinetic study of this system, which includes an SAR analysis, demonstrates that the reaction is highly tunable based on the ring substituents.

SUBMITTER: Topczewski JJ

PROVIDER: S-EPMC3685722 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Kinetic assessment of N-methyl-2-methoxypyridinium species as phosphonate anion methylating agents.

Topczewski Joseph J JJ Quinn Daniel M DM

Organic letters 20130214 5

Organophosphate nerve agents and pesticides are potent inhibitors of acetylcholinesterase (AChE). Although oxime nucleophiles can reactivate the AChE-phosphyl adduct, the adduct undergoes a reaction called aging. No compounds have been described that reactivate the aged-AChE adduct. A family of 2-methoxypyridinium species which reverse aging in a model system is presented. A kinetic study of this system, which includes an SAR analysis, demonstrates that the reaction is highly tunable based on th ...[more]

PMID: 23410111

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