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Synthesis of enantiopure non-natural α-amino acids using tert-butyl (2S)-2-[bis- (tert-butoxycarbonyl)amino]5-oxopentanoate as key-intermediate: The first synthesis of (S)-2-amino-oleic acid

Citation:

Constantinou-Kokotou V, Magrioti V, Markidis T, Kokotos G. Synthesis of enantiopure non-natural α-amino acids using tert-butyl (2S)-2-[bis- (tert-butoxycarbonyl)amino]5-oxopentanoate as key-intermediate: The first synthesis of (S)-2-amino-oleic acid. Journal of Peptide Research. 2001;58:325-331.

Abstract:

A general method for the synthesis of enantiopure non-natural α-amino acids is described. The key intermediate tert-butyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate was obtained from l-glutamic acid after suitable protection and selective reduction of the γ-methyl ester group by DIBALH. Wittig reaction of this chiral aldehyde with various ylides led to a variety of δ,ε-unsaturated α-amino acids. This methodology was applied to the synthesis of (S)-2-amino-oleic acid.

Notes:

Cited By :11Export Date: 18 January 2017