[Synthesis of N-acetylmuramoyl-L-alanyl-D-isoglutamine beta-aryl glycosides]

Abstract

Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and naphthyl-2 beta-glycosides, novel muramyl dipeptide derivatives with phenolic aglycones, was reported. The starting N-glucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha-glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta-glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the target glycopeptides.