{Reference Type}: Journal Article
{Title}: Chemical Synthesis of a Densely Functionalized Aminodisaccharide from Fusobacterium nucleatum ATCC 23726 O-Antigen.
{Author}: Ding M;Qin C;Sun W;Tian G;Zou X;Hu J;Yin J;
{Journal}: Org Lett
{Volume}: 26
{Issue}: 19
{Year}: 2024 May 17
{Factor}: 6.072
{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.