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

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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.

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

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Publication details

The article was received on 10 Oct 2019, accepted on 27 Nov 2019 and first published on 28 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC07915G
Chem. Commun., 2020, Advance Article

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

    G. Tian, C. Qin, Z. Liu, D. Shen, X. Zou, J. Fu, J. Hu, P. H. Seeberger and J. Yin, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC07915G

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