Efficient protocols for the synthesis of enantiopure γ-amino acids with proteinogenic side chains

✍ Scribed by Vassilios Loukas; Caterina Noula; Dr George Kokotos

• Book ID: 105360269
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 167 KB
• Volume: 9
• Category: Article
• ISSN: 1075-2617
• DOI: 10.1002/psc.458

✦ Synopsis

Abstract

The synthesis of enantiopure γ‐substituted γ‐amino acids with proteinogenic side chains, starting from the corresponding natural α‐amino acids, was studied. N‐Protected amino aldehydes containing various protective groups were prepared from the corresponding amino alcohols by oxidation with NaOCl in the presence of AcNH‐TEMPO and directly reacted with methyl, benzyl and tert‐butyl phosphoranylidene acetate to produce α, β‐unsaturated γ‐amino esters. Simultaneous hydrogenation of the double bond and removal of either the benzyl or benzyloxycarbonyl group led to N‐ or C‐protected γ‐amino acids in high yield. The enantiomeric purity was studied by ^1^H NMR analysis of Mosher amides and chiral HPLC analysis. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.