Two substituted piperidyl glycosides, the L-alanyl-o-glutamic acid derivative 22 and the L-alanyl-yo-glutamyl-L-lysine derivative 25, have been prepared as aza-analogues of the repeating disaccharide unit in peptidoglycan and screened as potential antibacterial agents. Starting from diacetoneglucose 1, the synthesis of an anomeric mixture of intermediate 5-0-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-3-0-(4-methoxybenzyl)-~-mannofuranosides 1 l a / l l p (a: p ratio -1 :1) is described. Their transformation into the 1,5-dideoxy-l,5-imino-~-mannitol 15 and its corresponding P-glycoside derivative 18, a common and advanced intermediate en route to the aza-analogues 22 and 25, is also described. Neither product showed any antibacterial activity. t Systematic name 1,5-dideoxy-1,5-imino-~-mannitol. * The two peptides, ~-ala-~-glu(OBn), ( [ a ] , + 18.3 (c 0.51, CHCI,)} and ~-ala-y-~-glu(OBn)-~-Lys(Z)OBn ([alD + 5.7 (c 1.0, CHCI,)), were synthesized in high yields by solution peptide-coupling methodology (DCC-HOBT-N-methylmorpholine). Their constituent, protected amino acids are either commercially available or easily prepared.
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