G. Auger et al., SYNTHESIS OF DIPEPTIDES CONTAINING PROPARGYLGLYCINE AND 2-AMINOPIMELIC ACID, Bulletin des Societes chimiques belges, 102(11-12), 1993, pp. 729-734
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.