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

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 Zemplen de-O-acetylation of benzyl chitinbioside peracetate leads to a fast and efficient route to N-acetylmuramyl beta(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%.

Automated summary

This study demonstrates a novel selective Zemplen de-O-acetylation of benzyl chitinbioside peracetate for the efficient synthesis of N-acetylmuramyl beta(1 -> 4) N-acetylglucosaminide disaccharide, a key component in the construction of peptidoglycan oligomers. Starting from benzyl chitinbioside, the NAG-NAM disaccharide pentapeptide was successfully prepared in seven steps with an overall yield of 12%.