SYNTHESIS OF DIPEPTIDES CONTAINING PROPARGYLGLYCINE AND 2-AMINOPIMELIC ACID

Two dipeptides containing antibacterial amino acids, 2-aminopimelic ac id (Apm) and propargylglycine (Pra), were synthesized : L-Pra-ambo-Apm (1) and ambo-Apm-L-Pra (2). 1 was easily obtained from the protected derivative resulting from the coupling (carbodiimide method) of Boc-L- Pra-OH with H-ambo-Apm(OBu(t))-OBu(t). For 2, we followed a synthesis scheme in which the epsilon-carboxyl group of Apm was unprotected: aft er the coupling of Boc-rac-Apm-N3 with H-L-Pra-OBu(t), mild acidolytic treatment afforded the desired dipeptide. 2 displayed weak antibacter ial activity against some species.