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  Total synthesis of legionaminic acid as basis for serological studies

Matthies, S., Stallforth, P., & Seeberger, P. H. (2015). Total synthesis of legionaminic acid as basis for serological studies. Journal of the American Chemical Society, 137(8), 2848-2851. doi:10.1021/jacs.5b00455.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0026-B82F-5 Version Permalink: https://hdl.handle.net/21.11116/0000-0007-E35A-4
Genre: Journal Article

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 Creators:
Matthies, Stefan1, Author           
Stallforth, Pierre2, Author           
Seeberger, Peter H.3, 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              
3Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 Abstract: Legionaminic acid is a nine-carbon diamino monosaccharide that is found coating the surface of various bacterial human pathogens. Its unique structure makes it a valuable biological probe, but access via isolation is difficult and no practical synthesis has been reported. We describe a stereoselective synthesis that yields a legionaminic acid building block as well as linker-equipped conjugation-ready legionaminic acid starting from cheap d-threonine. To set the desired amino and hydroxyl group pattern of the target, we designed a concise sequence of stereoselective reactions. The key transformations rely on chelation-controlled organometallic additions and a Petasis multicomponent reaction. The legionaminic acid was synthesized in a form that enables attachment to surfaces. Glycan microarray containing legionaminic acid revealed that human antibodies bind the synthetic glycoside. The synthetic bacterial monosaccharide is a valuable probe to detect an immune response to bacterial pathogens such as Legionella pneumophila, the causative agent of Legionnaire’s disease.

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 Dates: 2015-01-162015-02-102015
 Publication Status: Issued
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 Identifiers: ISI: 000350614700016
DOI: 10.1021/jacs.5b00455
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 137 (8) Sequence Number: - Start / End Page: 2848 - 2851 Identifier: ISSN: 0002-7863