Synthesis of P1-Citronellyl-P2-α- -pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG

P1-Citronellyl-P2-α- -pyranosyl pyrophosphates containing α- -N-acetylglucoseaminyl, α- -glucosyl, and α- -N-acetylmuramyl carbohydrates were synthesized and used in substrate specificity studies of the Escherichia coli MurG enzyme. Oxalyl chloride activation of citronellyl phosphate for coupling to α- -pyranose-1-phosphates resulted in markedly improved yields over traditional Khorana–Moffatt and diphenyl chlorophosphate activation strategies.