V. Constantinou-Kokotou, V. Magrioti, T. Markidis
Oct 1, 2001
Citations
0
Influential Citations
7
Citations
Journal
The journal of peptide research : official journal of the American Peptide Society
Abstract
A general method for the synthesis of enantiopure non-natural alpha-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 gamma-methyl ester group by DIBALH. Wittig reaction of this chiral aldehyde with various ylides led to a variety of delta,epsilon-unsaturated alpha-amino acids. This methodology was applied to the synthesis of (S)-2-amino-oleic acid.