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  Total syntheses of conjugation-ready repeating units of Acinetobacter baumannii AB5075 for glycoconjugate vaccine development

Zhang, S., & Seeberger, P. H. (2021). Total syntheses of conjugation-ready repeating units of Acinetobacter baumannii AB5075 for glycoconjugate vaccine development. Chemistry – A European Journal, 27(69), 17444-17451. doi:10.1002/chem.202103234.

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 Creators:
Zhang, Shuo1, Author              
Seeberger, Peter H.1, Author              
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              

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Free keywords: amides, carbohydrates, oligosaccharides, total synthesis, vaccines
 Abstract: Acinetobacter baumannii is an opportunistic pathogen that causes serious nosocomial infections. One of the multidrug-resistant strains, AB5075, can result in bacteremia, pneumonia and wound infections associated with high morbidity and mortality. The structurally unique glycans on the surface of these bacteria are attractive targets for the development of glycoconjugate vaccines. Here, we report the first total synthesis of the densely functionalized trisaccharide repeating unit of A. baumannii AB5075 as well as two analogues. The construction of 1,2- cis linkages between the rare sugars relies on a double-serial inversion strategy. The judicious selection of building blocks and reaction conditions allowed for stereoselective glycosylations, the installation of acetamido groups and the (S)-3-hydroxybutanoyl chain.

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Language(s): eng - English
 Dates: 2021-10-192021
 Publication Status: Published in print
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 Table of Contents: -
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 Identifiers: DOI: 10.1002/chem.202103234
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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 27 (69) Sequence Number: - Start / End Page: 17444 - 17451 Identifier: ISSN: 0947-6539