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Table 23.2 Reactive groups that can covalently react with the catalytically active serine.

From: Inhibitors of Hydrolases with an Acyl–Enzyme Intermediate

Inhibitor type

Functional group

 

Irreversible

Chloromethylketone

–COCH2Cl

Sulfonylfluoride

–SO2F

Estera

–COOR

Boronic acida

–B(OR)2

Reversible

Aldehyde

–CHO

Ketone

–COR (R = Alkyl, –Aryl)

Trifluoromethylketone

–COCF3

α-Ketocarboxylic acid

–COCOOH

α-Ketoamide

–COCONHR

α-Ketoester

–COCOOR

  1. aReversible as well as irreversible examples are known.