Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

Summary Some of the chemistry of amino acids going on in our laboratory (Laboratoire des Amino acides Peptides et Protéines) is described as well as some mass spectrometry methodology for their characterization particularly on solid supports. Several aspects are presented including: (i) the stereoselective synthesis of natural and unnatural amino acids using 2-hydroxypinan-3-one as chiral auxiliary; (ii) the stereoselective synthesis of natural and unnatural amino acids by deracemization of α -amino acids via their ketene derivatives; (iii) the synthesis of α -aryl- α -amino acids via reaction of organometallics with a glycine cation; (iv) the diastereoselective synthesis of glycosyl- α -amino acids; (v) the synthesis of β -amino acids using a-aminopyrrolidinopiperazinediones as chiral templates; (vi) the reactivity of urethane-N-protected N-carboxyanhydrides. To characterize natural and non natural amino acids through their immonium ions by mass spectrometry, some methodology is also described.