| Autor: |
Luo, Sheng, Xu, Zhuo-Jia, Wang, Xia, Hu, Xiao-Qing, Shang, Ke, Zhang, Zhen, He, Chao, Qin, Yong, Yang, Jin-Song |
| Zdroj: |
Organic Letters; September 2024, Vol. 26 Issue: 38 p8069-8073, 5p |
| Abstrakt: |
Acinetobacter baumanniiposes a serious threat to human health. Pathogenic bacterial lipopolysaccharides (LPSs) are potent immunogens for the development of antibacterial vaccines. To investigate the antigenic properties of A. baumanniiLPS, five well-defined core oligosaccharide fragments from the LPS of A. baumanniiSMAL and ATCC 19606 were synthesized. A divergent synthesis strategy based on orthogonally protected α-(2 → 5)-linked Kdo dimer 6was developed. Selective exposure of different positions in this key precursor and then elongation of sugar chains via stereocontrolled formation of both 1,2-transand 1,2-cis-2-aminoglycosidic linkages permitted the efficient synthesis of the targets. The synthetic route also highlights a 4-Oand then 7-Oglycosylation sequence for assembly of the novel 4,7-branched Kdo framework. Antigenicity assay using the glycan microarray technique disclosed that tetrasaccharide 3featuring both 4,7-branch and α-(2 → 5)-Kdo-Kdo structural elements was a potential antigenic determinant. |
| Databáze: |
Supplemental Index |
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