Lysine analogues-
chloromethyl ketones

In 1981, a medicinal chemist at Bayer in Wuppertal, Germany (Reinhardt, Ann. N.Y. Acad. Sci. 1981, 370:836.) designed a series of direct-acting Factor XIIIa inhibitors. According to the author, the molecule combines the substrate amine architecture (lysine co-substrate) with the chemical reactivity of the sulfhydryl reagent (active site cysteine attacking the chloromethyl ketone). The compound inhibits tissue transglutaminase as well.

Lysine analogues reaction machanism