FunctionaIized erythro N-protected α-amino epoxides. Stereocontrolled synthesis and biological activity

Amnon Albeck, Gary I. Estreicher

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Erythro N-protected α-amino epoxides, derived from α-amino acids bearing functionalized side chains, were synthesized. The key synthetic step is a stereoselective reduction of the corresponding haloketone either to the halohydrin or directly to the epoxide. The side chains include ester, ether and alcohol, nitro guanidine, carbamate and amine functional groups, derived from aspartate and glutamate, serine, arginine, and lysine, respectively. The epoxides derived from lysine and N(ω)-nitro-arginine exhibited selective inactivation of the cysteine proteases papain and cathepsin B, while they failed to inactivate the serine protease trypsin.

Original languageEnglish
Pages (from-to)5325-5338
Number of pages14
JournalTetrahedron
Volume53
Issue number14
DOIs
StatePublished - 7 Apr 1997

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