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

Tian, Guangzong; Qin, Chunjun; Liu, Zhonghua; Shen, Dacheng; Zou, Xiaopeng; Fu, Junjie; Hu, Jing; Seeberger, Peter H.; Yin, Jian

doi:10.1039/C9CC07915G

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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;

/persons/resource/persons244010

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

/persons/resource/persons214142

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

/persons/resource/persons121849

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

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

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: https://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.