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Issue 3, 2020
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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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Article information


Submitted
10 Oct 2019
Accepted
27 Nov 2019
First published
28 Nov 2019

Chem. Commun., 2020,56, 344-347
Article type
Communication

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, 56, 344
DOI: 10.1039/C9CC07915G

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