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Synthesis of a β-Ketophosphonate Bioisostere of UDP-N-acetylglucosamine



A concise route to a new β-ketophosphonate analog of glycosyl nucleotides is described. Such a diphosphate bioisostere is a stable mimic of enzyme substrates involved in peptidoglycan biosynthesis and will be the starting point for the development of new potential antibiotics. The synthesis is carried out by condensing a lithiomethylenephosphonate derivative on a methyl N-acetylglucosaminylacetate followed by esterification with a uridine derivative. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)