Synthesis of an analogue of the lipoglycopeptide membrane intermediate I of peptidoglycan biosynthesis

α-Dihydroheptaprenyl-pyrophosphoryl- N-acetylmuramoyl-L-Ala-γ-D-Glu- meso-diaminopimeloyl(N∈-dansyl)-D-Ala-D-Ala ( 1), an analogue of lipid I ofpeptidoglycan biosynthesis, was synthesized from natural UDP-N-acetylmuramoyl-pentapeptide in three steps. Compound 1 was shown to be asubstrate for the MurG transferase from Escherichia coli, even in theabsence of membranes. When membranes were present, dansylated peptidoglycanwas also formed.