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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0005-8749-1 Version Permalink: https://hdl.handle.net/21.11116/0000-0006-56B6-C
Genre: Journal Article

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Article.pdf (Publisher version), 4MB
 
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 Creators:
Tian, Guangzong1, Author
Qin, Chunjun, Author
Liu, Zhonghua, Author
Shen, Dacheng1, Author           
Zou, Xiaopeng2, Author           
Fu, Junjie, Author
Hu, Jing, Author
Seeberger, Peter H.1, Author           
Yin, Jian, Author
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              
2Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863286              

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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.

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Language(s): eng - English
 Dates: 2019-11-282020
 Publication Status: Issued
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1039/C9CC07915G
BibTex Citekey: C9CC07915G
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Title: Chemical Communications
  Other : Chem. Commun.
Source Genre: Journal
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Publ. Info: Cambridge, UK : Royal Society of Chemistry
Pages: - Volume / Issue: 56 (3) Sequence Number: - Start / End Page: 344 - 347 Identifier: ISSN: 1359-7345