A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis. Issue 12 (5th October 2021)

• Record Type: Journal Article
• Authors: Rousseau, Antoine; Richard, Emeline; Jeacomine, Isabelle; Armand, Sylvie; Fort, Sébastien; Cottaz, Sylvain
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 12(2021)
• Page Start: 3290
• Page End: 3292
• Publication Date: 2021-10-05
• Subjects: peptidoglycan -- muropeptide -- oligosaccharide -- chitinbiose -- selective deacylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100547
• Languages: English
• ISSNs: 2193-5807

Abstract

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%. Abstract : A NAG‐NAM disaccharide pentapeptide precursor of peptidoglycan oligomers is prepared in 6 steps from β‐benzyl chitinbioside with 12% overall yield.