Synthetic Sialosides Terminated with 8‐ N ‐Substituted Sialic Acid as Selective Substrates for Sialidases from Bacteria and Influenza Viruses
Abstract: Sialosides containing C8‐modified sialic acids are challenging synthetic targets but potentially useful probes for diagnostic substrate profiling of sialidases and elucidating the binding specificity of sialic acid‐interacting proteins. Here, we demonstrate efficient chemoenzymatic methods for synthesizing para‐nitrophenol‐tagged α2–3‐ and α2–6‐linked sialyl galactosides containing C8‐acetamido, C8‐azido, or C8‐amino derivatized N‐acetylneuraminic acid (Neu5Ac). High‐throughput substrate specificity studies showed that the C8‐modification of sialic acid significantly changes its recognition by sialidases from humans, various bacteria, and different influenza A and B viruses. Sialosides carrying Neu5Ac with a C8‐azido modification were generally well tolerated by all the sialidases we tested, whereas sialosides containing C8‐acetamido‐modified Neu5Ac were only cleaved by selective bacterial sialidases. In contrast, sialosides with C8‐amino‐modified Neu5Ac were cleaved by a combination of selective bacterial and influenza A virus sialidases. These results indicate that sialosides terminated with a C8‐amino or C8‐acetamido‐modified sialic acid can be used with other sialosides for diagnostic profiling of disease‐causing sialidase‐producing pathogens.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Synthetic Sialosides Terminated with 8‐ N ‐Substituted Sialic Acid as Selective Substrates for Sialidases from Bacteria and Influenza Viruses ; day:14 ; month:06 ; year:2024 ; extent:10
Angewandte Chemie / International edition. International edition ; (14.06.2024) (gesamt 10)
- Creator
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Mishra, Bijoyananda
Yuan, Yue
Yu, Hai
Kang, Hyeog
Gao, Jin
Daniels, Robert
Chen, Xi
- DOI
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10.1002/anie.202403133
- URN
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urn:nbn:de:101:1-2406141426559.007844982473
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:50 AM CEST
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Mishra, Bijoyananda
- Yuan, Yue
- Yu, Hai
- Kang, Hyeog
- Gao, Jin
- Daniels, Robert
- Chen, Xi
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Selective hydrodeoxygenation of carbonyl-substituted aromatic substrates using multifunctional catalysts
Regioselectivity of the SEAr-based cyclizations and SEAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles
Replication of avian, human and swine influenza viruses in porcine respiratory explants and association with sialic acid distribution
Role of substrates morphology and chemistry in ALD HfO₂ on Si(111)-H terminated surfaces as model
Analysis of the sialic acid binding activity of the hemagglutinins of influenza viruses and its role in host tropism
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Gold Nanoparticles Decorated with Sialic Acid Terminated Bi‐antennary N‐Glycans for the Detection of Influenza Virus at Nanomolar Concentrations †
Selective hydrodeoxygenation of carbonyl-substituted aromatic substrates using multifunctional catalysts
Regioselectivity of the SEAr-based cyclizations and SEAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles
Replication of avian, human and swine influenza viruses in porcine respiratory explants and association with sialic acid distribution
Role of substrates morphology and chemistry in ALD HfO₂ on Si(111)-H terminated surfaces as model
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