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. Author manuscript; available in PMC: 2015 Mar 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Jan 23;53(9):2312–2330. doi: 10.1002/anie.201307761

Scheme 1.

Scheme 1

Proposed mechanism for the inactivation of the proteasome by epoxomicin. Initial hemiketal formation is followed by epoxide opening by the terminal amine, to form a stable morpholine adduct, which has been observed through x-ray crystallography.[29]