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

✍ Scribed by Amnon Albeck; Gary I. Estreicher

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
753 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Erythro N-protected a-amino epoxides, derived from s-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 Nar-nitro-arginine exhibited selective inactivation of the cysteine proteases papain and cathepsin B, while they failed to inactivate the serine protease trypsin.

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