title: Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG.
abstract: P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates containing alpha-D-N-acetylglucoseaminyl, alpha-D-glucosyl, and alpha-D-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 alpha-D-pyranose-1-phosphates resulted in markedly improved yields over traditional Khorana-Moffatt and diphenyl chlorophosphate activation strategies.
authors.affiliation: Johnson Research Foundation and the Department of Biochemistry and Biophysics, The University of Pennsylvania School of Medicine, Philadelphia, PA 19104-6059, USA.
authors.forename: P
authors.initials: P
authors.lastname: Cudic
authors.forename: D C
authors.initials: DC
authors.lastname: Behenna
authors.forename: M K
authors.initials: MK
authors.lastname: Yu
authors.forename: R G
authors.initials: RG
authors.lastname: Kruger
authors.forename: L M
authors.initials: LM
authors.lastname: Szewczuk
authors.forename: D G
authors.initials: DG
authors.lastname: McCafferty
mesh_terms: D001425:Bacterial Outer Membrane Proteins; D011756:Diphosphates / Q000138:chemical synthesis* / Q000378:metabolism; D004926:Escherichia coli / Q000201:enzymology*; D009682:Magnetic Resonance Spectroscopy; D017351:N-Acetylglucosaminyltransferases / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D013379:Substrate Specificity
chemical_list: D001425:Bacterial Outer Membrane Proteins; D011756:Diphosphates; D017351:N-Acetylglucosaminyltransferases; C064057:UDP-N-acetylglucosamine-N-acetylmuramyl-(pentapeptide)pyrophosphoryl-undecaprenol N-acetylglucosamine transferase