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Total synthesis of the Helicobacter pylori serotype O2 O-antigen α-(1 → 2)- and α-(1 → 3)-linked oligoglucosides

MPS-Authors

Tian,  Guangzong
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Shen,  Dacheng
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Zou,  Xiaopeng
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Tian, G., Qin, C., Liu, Z., Shen, D., Zou, X., Fu, J., et al. (2020). Total synthesis of the Helicobacter pylori serotype O2 O-antigen α-(1 → 2)- and α-(1 → 3)-linked oligoglucosides. Chemical Communications, 56(3), 344-347. doi:10.1039/C9CC07915G.


Cite as: http://hdl.handle.net/21.11116/0000-0005-8749-1
Abstract
Exploiting synergistic remote participation effects of acyl groups at the O3 and O6 positions was key to the complete α-selectivity during the total synthesis of the unique (1 → 2)- and (1 → 3)-linked α-oligoglucosides from the Helicobacter pylori O2 O-antigen. Acyl remote participation and solvent effects were found to counteract during α-stereoselective glucosylations for the first time. The resulting antigen is a lead for the development of a carbohydrate-conjugate vaccine.