ArticleCarbohydrate research2014
Chemoenzymatic synthesis of sialosides containing C7-modified sialic acids and their application in sialidase substrate specificity studies.
Article in Carbohydrate research, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 31 citations in OpenAlex.
- Exploring the Scope of FunctionalizedMolecules (Basel, Switzerland) · 2025Article
- Synthesis of 4-azido sialic acid for testing against Siglec-7 and in metabolic oligosaccharide engineering.RSC chemical biology · 2025Article
- Synthetic Sialosides Terminated with 8-N-Substituted Sialic Acid as Selective Substrates for Sialidases from Bacteria and Influenza Viruses.Angewandte Chemie (International ed. in English) · 2024Article
- Enabling Chemoenzymatic Strategies and Enzymes for Synthesizing Sialyl Glycans and Sialyl Glycoconjugates.Accounts of chemical research · 2024Article
- Sialosides Containing 7-ACS infectious diseases · 2023Article
- One-pot multienzyme (OPME) chemoenzymatic synthesis of brain ganglioside glycans with human ST3GAL II expressed inChemCatChem · 2022Article
- Facile and Scalable Route to Access Rare Deoxy Amino Sugars for Nonulosonic Acid Aldolase Biosynthesis.Frontiers in chemistry · 2022Article
- 7-Fluorosialyl Glycosides Are Hydrolysis Resistant but Readily Assembled by Sialyltransferases Providing Easy Access to More Metabolically Stable Glycoproteins.ACS central science · 2021Article
- A Chemoenzymatic Synthon Strategy for SynthesizingThe Journal of organic chemistry · 2020Article
- Catalytic Cycle ofBiochemistry · 2020Article
- Therapeutic CMP-Nonulosonates against Multidrug-ResistantJournal of immunology (Baltimore, Md. : 1950) · 2020Article
- L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues.Organic & biomolecular chemistry · 2020Article
- Strategies for chemoenzymatic synthesis of carbohydrates.Carbohydrate research · 2019Review
- SnClBeilstein journal of organic chemistry · 2019Article
- Natural and Synthetic Sialylated Glycan Microarrays and Their Applications.Frontiers in molecular biosciences · 2019Review
- α2-6-Neosialidase: A Sialyltransferase Mutant as a Sialyl Linkage-Specific Sialidase.ACS chemical biology · 2018Article
- A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides.Angewandte Chemie (International ed. in English) · 2018Article
- Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors.ACS catalysis · 2018Article
- Converting Pasteurella multocidaα2-3-sialyltransferase 1 (PmST1) to a regioselective α2-6-sialyltransferase by saturation mutagenesis and regioselective screening.Organic & biomolecular chemistry · 2017Article
- Chemoenzymatic synthesis of para-nitrophenol (pNP)-tagged α2-8-sialosides and high-throughput substrate specificity studies of α2-8-sialidases.Organic & biomolecular chemistry · 2016Article
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7 authors at 1 institution in 1 country.
Funding
Abstract
Modifications at the glycerol side chain of sialic acid in sialosides modulate their recognition by sialic acid-binding proteins and sialidases. However, limited work has been focused on the synthesis and functional studies of sialosides with C7-modified sialic acids. Here we report chemical synthesis of C4-modified ManNAc and mannose and their application as sialic acid precursors in a highly efficient one-pot three-enzyme system for chemoenzymatic synthesis of α2-3- and α2-6-linked sialyl para-nitrophenyl galactosides in which the C7-hydroxyl group in sialic acid (N-acetylneuraminic acid, Neu5Ac, or 2-keto-3-deoxynonulosonic acid, Kdn) was systematically substituted by -F, -OMe, -H, and -N3 groups. Substrate specificity study of bacterial and human sialidases using the obtained sialoside library containing C7-modified sialic acids showed that sialosides containing C7-deoxy Neu5Ac were selective substrates for all bacterial sialidases tested but not for human NEU2. The information obtained from sialidase substrate specificity can be used to guide the design of new inhibitors that are selective against bacterial sialidases.
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