PMID: 11606217Oct 19, 2001Paper

Synthesis of enantiopure non-natural alpha-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

The Journal of Peptide Research : Official Journal of the American Peptide Society
Violetta Constantinou-KokotouGeorge Kokotos

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.

References

Jul 1, 1997·Journal of Peptide Science : an Official Publication of the European Peptide Society·A NicolaouW A Gibbons
Jan 5, 1999·Bioorganic & Medicinal Chemistry Letters·G KokotosC Roussakis
Jul 10, 1999·Amino Acids·V Constantinou-Kokotou, G Kokotos

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Citations

Feb 5, 2003·Bioorganic & Medicinal Chemistry Letters·Victoria MagriotiVioletta Constantinou-Kokotou
Sep 30, 2008·Bioorganic & Medicinal Chemistry Letters·Victoria MagriotiGeorge Kokotos
Jan 7, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Violetta Constantinou-KokotouEdward A Dennis
Mar 13, 2012·Journal of Chromatographic Science·Octavian CălinescuElena Pincu
Jan 9, 2004·Journal of Medicinal Chemistry·Victoria MagriotiVioletta Constantinou-Kokotou

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