UPR 5301

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

19 November 2021

The Chemistry and Biotechnology team of CERMAV has just published a very efficient methodological approach for the synthesis of the repeating unit of peptidoglycan, an essential constituent of the bacterial cell wall whose biosynthesis is targeted by most antibiotics. This first result is the basis of a global strategy for accessing synthetic peptidoglycan oligomers, fundamental tools to decipher the life cycle of this complex polymer. Click on the title for more information.

Abstract:
« 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%. »

The paper is available (open access) over here.