Biochemistry 4th Edition by Reginald Garrett, Charles Grisham

Exercise 1

Characterizing a covalent enzyme inhibitor
Tosyl-L-phenylalanine chloromethylketone (TPCK) specifically inhibits chymotrypsin by covalently labeling His 57.
a. Propose a mechanism for the inactivation reaction, indicating the structure of the product(s).
b. State why this inhibitor is specific for chymotrypsin.
c. Propose a reagent based on the structure of TPCK that might be an effective inhibitor of trypsin.