Article

Letters in Peptide Science

, Volume 4, Issue 4, pp 371-376

First online:

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

  • Geneviève AugerAffiliated withURA 1131, Université de Paris-Sud
  • , Muriel CrouvoisierAffiliated withURA 1131, Université de Paris-Sud
  • , Martine CaroffAffiliated withURA 1116, CNRS, Université de Paris-Sud
  • , Jean van HeijenoortAffiliated withURA 1131, Université de Paris-Sud
  • , Didier BlanotAffiliated withURA 1131, Université de Paris-Sud

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Summary

α-Dihydroheptaprenyl-pyrophosphoryl-N-acetylmuramoyl-L-Ala-γ-D-Glu-meso-diaminopimeloyl(N -dansyl)-D-Ala-D-Ala (1), an analogue of lipid I of peptidoglycan biosynthesis, was synthesized from natural UDP-N-acetylmuramoyl-pentapeptide in three steps. Compound1 was shown to be a substrate for the MurG transferase fromEscherichia coli, even in the absence of membranes. When membranes were present, dansylated peptidoglycan was also formed.

Keywords

Dansyl group α-Dihydroheptaprenyl phosphate MurG Phosphoroimidazolidate method Plasma desorption mass spectrometry UDP-N-acetylmuramoyl-pentapeptide