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 alpha-amino acids via their ketene derivatives; (iii) the synthesis of alpha-aryl-alpha-amino acids via reaction of organometallics with a glycine cation; (iv) the diastereoselective synthesis of glycosyl-alpha-amino acids; (v) the synthesis of beta-amino acids using alpha-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.

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Diastereoselective Synthesis of Glycosyl-α-amino Acids.-Some glycosyl-α-amino acid derivatives such as (IV) and (IX) are prepared via coupling of the sugar (I) with the amino esters (II) and (VII). Interestingly, treatment of (I) with (VII) does not yield the expected condensation product but the spirooxazolidine (VIII). In the presence of BOP/iPr 2 NEt the amino acid derived from the amino ester (IIIa) easily undergoes spirolactonization to the compound (V), which undergoes purely O-acyl ring opening with NH 3 . -(BOUIFRADEN, S.; LAVERGNE, J.-P.; MARTINEZ, J.; VIALLEFONT, P.; RICHE, C.; Tetrahedron: Asymmetry 8 (1997) 6, 949-955; Lab. Chim. Biomol., CNRS, Univ. Montpellier II, F-34095 Montpellier, Fr.; EN)