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

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%.
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https://hal.archives-ouvertes.fr/hal-03374259
Contributor : Sébastien Fort Connect in order to contact the contributor
Submitted on : Tuesday, October 12, 2021 - 2:14:39 PM
Last modification on : Thursday, December 2, 2021 - 2:14:02 PM
Long-term archiving on: : Thursday, January 13, 2022 - 7:39:07 PM

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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, Wiley, inPress, ⟨10.1002/ajoc.202100547⟩. ⟨hal-03374259⟩

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