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• W2043137724 startingPage "2848" @default.
• W2043137724 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." @default.
• W2043137724 created "2016-06-24" @default.
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• W2043137724 date "2015-02-19" @default.
• W2043137724 modified "2023-10-10" @default.
• W2043137724 title "Total Synthesis of Legionaminic Acid as Basis for Serological Studies" @default.
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• W2043137724 doi "https://doi.org/10.1021/jacs.5b00455" @default.
• W2043137724 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25668389" @default.
• W2043137724 hasPublicationYear "2015" @default.
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