A New Route to NAG‐NAM Disaccharide, an Important Building Block for Peptidoglycan Oligomer Synthesis
| Autor: | Isabelle Jeacomine, Sylvie Armand, Emeline Richard, Sébastien Fort, Sylvain Cottaz, Antoine Rousseau |
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| Přispěvatelé: | Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Université Grenoble Alpes (UGA)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Disaccharide Oligosaccharide peptidoglycan 010402 general chemistry 01 natural sciences Pentapeptide repeat Oligomer chitinbiose Bacterial cell structure 0104 chemical sciences carbohydrates (lipids) chemistry.chemical_compound Enzyme muropeptide oligosaccharide selective deacylation Peptidoglycan |
| Zdroj: | Asian Journal of Organic Chemistry Asian Journal of Organic Chemistry, Wiley, In press, ⟨10.1002/ajoc.202100547⟩ |
| ISSN: | 2193-5807 2193-5815 |
| Popis: | International audience; 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%. |
| Databáze: | OpenAIRE |
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