New Chiral Synthons of 13C- or 15N-labelled α-amino acids

Conference poster, 2006

Easily available chiral synthons of α-amino acids selectively labelled with 13C or 15N could significantly simplify preparation of enantiomerically pure selectively isotopically substituted α-amino acids for NMR and MS studies of biological systems. Based on previously described preparation of labelled synthons of nucleophilic and electrophilic glycine, different approaches to labelled quaternary α-amino acids were evaluated. In the case of α-(13C)methyl α-amino acids, two alternatives exists: 1. preparation of an alanine synthon by introduction of the α-(13C)methyl group into a glycine synthon followed by an attachment of a side chain; 2. usage of α-amino acids synthons carrying a side chain and introduction of the α-(13C)methyl group. The second approach was found to be better suited for the preparative applications. An optimisation was done in order to increase yields and decrease release of by-products to waste water.