Mesh : Fusobacterium nucleatum / chemistry O Antigens / chemistry Molecular Structure Disaccharides / chemistry chemical synthesis

来  源:   DOI:10.1021/acs.orglett.4c01344

Abstract:
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.
摘要:
具核梭杆菌,结直肠癌相关的微生物,可以触发或加速多种病理。我们报告了从F.nucleatumATCC23726O-抗原中首次合成含有六个氨基的缀合就绪二糖。稀有的2,3-二氨基-d-葡萄糖醛酸酰胺和2-乙酰氨基-4-氨基-d-岩藻糖由d-葡萄糖胺通过构型转化合成,亲核取代,C6氧化,和C6脱氧。保护基团和反应条件的明智选择能够选择性地安装N-乙酰基,N-丙酰基,N-甲酰基,和羧酰胺基。
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