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J Med Chem. 2002 Nov 7;45(23):4958-60.

Aza-peptide epoxides: a new class of inhibitors selective for clan CD cysteine proteases.

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  • 1School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta 30332-0400, USA.


Aza-peptide epoxides, a new class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. The inhibitors have second-order rate constants up to 10(5) M(-1) s(-1), with the most potent epoxides having the S,S stereochemistry. The aza-Asn derivatives are effective legumain inhibitors, while the aza-Asp epoxides were specific for caspases. The inhibitors have little or no inhibition with other proteases such as chymotrypsin, papain, or cathepsin B.

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