Total synthesis of zwitterionic PS A2 oligosaccharides from Bacteroides fragilis
Year: 2025
Type: article
Abstract: Zwitterionic polysaccharides have unique structures and can elicit T cell–dependent immune responses. To unravel their molecular mode of action and develop potential alternatives for carrier proteins in carbohydrate-based vaccines, we here describe a total synthesis of zwitterionic PS A2 oligosaccharides from Bacteroides fragilis . The pentasaccharide and decasaccharide bearing one or two repeating units were efficiently synthesized via convergent glycosylation strategy. The ingenious protecting groups have enabled the stereoselectivity of glycosylation. A unique synthetic approach was developed to introduce the chiral 3-hydroxybutanoic acid side chain on mannoheptose, which proved very challenging to form in this skeleton.
Source: Science Advances
Authors: Xinxin Li, Qingzhi Pan-Gao, Yongyong Wan, Fuxing Zeng, Jianying Qi, Yuanhong Tu, Liming Wang, Zhen Wang, Jeroen D. C. Codée, Qingju Zhang
Institutions: Jiangxi Normal University, Leiden University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $4,500
OpenAlex ID: W4417283846