Chemical Synthesis of the Trisaccharide Repeating Unit of the O‑Antigen of Fusobacterium nucleatum ATCC 51191

Herein, the trisaccharide repeating unit of Fusobacterium nucleatum ssp. animalis ATCC 51191, which is used to develop oncomicrobial vaccines, was efficiently synthesized for the first time. The synthetic approach featured the following: (i) construction of the 1,2-cis-glycosidic linkage using the l...

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Bibliographic Details
Published in:Organic letters 2024-01, Vol.26 (1), p.321-326
Main Authors: Sun, Wenbin, Tian, Guangzong, Ding, Meiru, Zou, Xiaopeng, Hu, Jing, Yin, Jian
Format: Article
Language:English
Subjects:
Fusobacterium
Fusobacterium nucleatum
O Antigens
Trisaccharides
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Summary:Herein, the trisaccharide repeating unit of Fusobacterium nucleatum ssp. animalis ATCC 51191, which is used to develop oncomicrobial vaccines, was efficiently synthesized for the first time. The synthetic approach featured the following: (i) construction of the 1,2-cis-glycosidic linkage using the large steric hindrance of a phthalimide group at C4 of fucosamine; (ii) synthesis of the trisaccharide via a linear [2 + 1] glycosylation strategy; and (iii) installation of l-alanine using hexafluorophosphate azabenzotriazole tetramethyl uronium as a promoter.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03981