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Chemical Synthesis of a Densely Functionalized Aminodisaccharide from Fusobacterium nucleatum ATCC 23726 O-Antigen.

Meiru DingChunjun QinWenbin SunGuangzong TianXiaopeng ZouJing HuJian Yin
Published in: Organic letters (2024)
Fusobacterium nucleatum , a colorectal-cancer-associated oncomicrobe, can trigger or accelerate numerous pathologies. We report the first synthesis of a conjugation-ready disaccharide containing six amino groups from F. nucleatum ATCC 23726 O-antigen. Rare 2,3-diamido-d-glucuronic acid amide and 2-acetamido-4-amino-d-fucose were synthesized from d-glucosamine through configuration inversion, nucleophilic substitution, C6 oxidation, and C6 deoxygenation. A judicious choice of protecting groups and reaction conditions enabled the selective installation of N -acetyl, N -propanoyl, N -formyl, and carboxamido groups.
Keyphrases
  • quantum dots
  • contrast enhanced
  • molecularly imprinted
  • high resolution
  • liquid chromatography