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Chemoenzymatic resolution of rac-malathion

Chemoenzymatic resolution of rac-malathion

David M Hitt, Yamina Belabassi, Joyce Suhy, Clifford E Berkman, Charles M Thompson

Tetrahedron Asymmetry. 2014 Apr 15;25(6-7):529-533.

PMID: 24839353

Abstract:

Malathion, diethyl 2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate, is an organophosphate used to control insect pests. Malathion contains a diethyl succinate moiety that is a known functional group susceptible to desymmetrizing enzymes such as esterases that selectively react with a single enantiomer. Purified rac-malathion was subjected to hydrolysis at the diethyl succinate moiety of malathion under various conditions using wild type pig liver esterase to form (S)-malathion (12 % ee) and ~ 3:2 mixture of α- and β-monoacids of (R)-malathion. Technical malathion could not be enriched due to the presence of esterase inhibitors. Further investigation of this resolution using a panel of six PLE isoenzymes also demonstrated formation of (S)-malathion, however, an improvement of up to 56 % ee was obtained.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP123251	Diethyl succinate		123-25-1	Price

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