Chemical synthesis of a synthetically useful L-galactosaminuronic acid building block.
10.1016/S1875-5364(22)60149-3
- Author:
Chun-Jun QIN
1
;
Hong-Li HOU
1
;
Mei-Ru DING
1
;
Yi-Kuan QI
1
;
Guang-Zong TIAN
1
;
Xiao-Peng ZOU
1
;
Jun-Jie FU
1
;
Jing HU
2
;
Jian YIN
3
Author Information
1. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China.
2. Wuxi School of Medicine, Jiangnan University, Wuxi 214122, China.
3. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China. Electronic address: murielle.jianyin@jiangnan.edu.cn.
- Publication Type:Journal Article
- Keywords:
C6 oxidation;
Chemical synthesis;
Glycal addition;
L-galactosaminuronic acid;
Orthogonal protection
- MeSH:
Carbohydrates;
Glycosides;
Oligosaccharides;
Oxidation-Reduction;
Polysaccharides/chemistry*
- From:
Chinese Journal of Natural Medicines (English Ed.)
2022;20(5):387-392
- CountryChina
- Language:English
-
Abstract:
Most bacterial cell surface glycans are structurally unique, and have been considered as ideal target molecules for the developments of detection and diagnosis techniques, as well as vaccines. Chemical synthesis has been a promising approach to prepare well-defined oligosaccharides, facilitating the structure-activity relationship exploration and biomedical applications of bacterial glycans. L-Galactosaminuronic acid is a rare sugar that has been only found in cell surface glycans of gram-negative bacteria. Here, an orthogonally protected L-galactosaminuronic acid building block was designed and chemically synthesized. A synthetic strategy based on glycal addition and TEMPO/BAIB-mediated C6 oxidation served well for the transformation of commercial L-galactose to the corresponding L-galactosaminuronic acid. Notably, the C6 oxidation of the allyl glycoside was more efficient than that of the selenoglycoside. In addition, a balance between the formation of allyl glycoside and the recovery of selenoglycoside was essential to improve efficiency of the NIS/TfOH-catalyzed allylation. This synthetically useful L-galactosaminuronic acid building block will provide a basis for the syntheses of complex bacterial glycans.
