A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis

Antoine Rousseau (1) , Emeline Richard (1) , Isabelle Jeacomine (1) , Sylvie Armand (1) , Sébastien Fort (1) , Sylvain Cottaz (1)

1 CERMAV - Centre de Recherches sur les Macromolécules Végétales

Peptidoglycan oligomers constitute precious tools for the biochemical and structural studies of enzymes involved in the bacterial cell wall metabolism. In this study we show that an unprecedented selective Zemplén de-O-acetylation of benzyl chitinbioside peracetate leads to a fast and efficient route to N-acetylmuramyl β(1→4) N-acetylglucosaminide disaccharide, a central building block for the synthesis of peptidoglycan oligomers. Starting from known benzyl chitinbioside, NAG-NAM disaccharide pentapeptide is prepared in seven steps with an overall yield of 12%.

Mots clés: peptidoglycan; muropeptide; oligosaccharide; chitinbiose; selective deacylation

Domaines: Chimie organique

Antoine Rousseau, Emeline Richard, Isabelle Jeacomine, Sylvie Armand, Sébastien Fort, et al.. A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis. Asian Journal of Organic Chemistry, 2021, 10 (12), pp.3290-3292. ⟨10.1002/ajoc.202100547⟩. ⟨hal-03374259⟩