Synthesis of epoxy and aziridino malonyl peptidomimetics

Short malonyl dehydro peptides have been epoxidized using H₂O₂/Na₂WO₄ dihydrate. The obtained diastereomeric epoxides were separated by HPLC and successfully tested in the ring opening reaction with N-Boc l-cysteine methyl ester, to indicate their electrophilic behavior. Moreover, by a simple two-step reaction, the epoxy malonyl peptides can be converted into the corresponding aziridino malonyl peptides.