Reactions of L-α-Tosylamino-β-propiolactone. II. A Novel Synthesis of L-Seryl Peptides

Abstract

Optically active α-tosylamino-β-propiolactone (III) was synthesized from N-tosyl-L-asparagine via L-2-tosylamino-3-aminopropionic acid. The β-propiolactone (III) reacted with amino acid esters or peptide esters in organic solvents to form L-seryl peptide esters in good yields. Racemization did not actually occur during the peptide coupling reaction.