Total Synthesis of the Conjugation-Ready Hexasaccharides of Pseudomonas aeruginosa Serotype O17 O-Antigen via One-Pot Glycosylation
Guangzong Tian
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorJialong Bao
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorGuodong Chen
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorXiaopeng Zou
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorChunjun Qin
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorJing Hu
Wuxi School of Medicine & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorCorresponding Author
Jian Yin
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
School of Life Sciences and Health Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
E-mail: [email protected]Search for more papers by this authorGuangzong Tian
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorJialong Bao
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorGuodong Chen
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorXiaopeng Zou
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorChunjun Qin
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorJing Hu
Wuxi School of Medicine & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
Search for more papers by this authorCorresponding Author
Jian Yin
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education & Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
School of Life Sciences and Health Engineering, Jiangnan University, Wuxi, Jiangsu, 214122 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
The eradication of Pseudomonas aeruginosa infections is becoming increasingly complex due to the emergence of multidrug-resistant strains, underscoring the urgent need for novel therapeutic strategies. Currently, no vaccine is available to prevent P. aeruginosa infections and the development of glycoconjugate vaccines based on P. aeruginosa lipopolysaccharides (LPS) presents significant challenges. To explore the immunological activity of the serotype O17 O-antigen, we present the first chemical synthesis of two hexasaccharides derived from the O17 O-antigen of P. aeruginosa, which possess distinct sequences. The synthesis of these two target hexasaccharides was accomplished using a chemoselective one-pot [2+2+2] assembly strategy and a common step-wise synthesis, respectively. The formation of β-mannosamine glycosidic linkages in products 1 and 2, was achieved through a direct stereoselective 1,2-cis-glycosylation involving 4,6-O-benzylidene-induced conformational locking facilitated by Ph2SO/Tf2O pre-activation, and an indirect 1,2-trans-β-glycosylation alongside SN2 substitution of azide groups at C2, respectively. The efficient synthesis of these conjugation-ready oligosaccharides from the O-antigen of P. aeruginosa serotype O17 will provide foundational materials for identifying key antigens and developing glycoconjugate vaccines.
Supporting Information
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Appendix S1: Supporting Information |
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