Chemistry, Department of: Faculty Series

 

David Berkowitz Publications

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Document Type

Article

Date of this Version

1995

Citation

J Org Chem. 1995 September ; 60(17): 5368–5369

Comments

Copyright 1995 Am. Chem. Soc.

doi:10.1021/jo00122a002

Abstract

Analogues of natural amino acids, in which the α-proton is replaced by an unsubstituted epoxide ring, are potential mechanism-based inhibitors for pyridoxal phosphate dependent enzymes.1 Yet, free α-oxiranyl amino acids have remained elusive until now. The synthesis of an α-(phenyl-substituted)oxiranyl amino ester has been reported. However, the accessibility and stability of the corresponding free, zwitterionic α-oxiranyl amino acid remained an open question.9

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