ArticleCarbohydrate research2017
Chemoenzymatic synthesis of Neu5Ac9NAc-containing α2-3- and α2-6-linked sialosides and their use for sialidase substrate specificity studies.
Article in Carbohydrate research, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 33 citations in OpenAlex.
- Catch, Cut, or Block? Versatile 4-N-Derivatized Sialyl Glycosides for Influenza Virus Neuraminidase Detection and Purification.Angewandte Chemie (International ed. in English) · 2025Article
- Asialoglycoprotein receptor 1: a multifaceted receptor in the liver and cardiovascular system.Frontiers in medicine · 2025Review
- Cellular sialoglycans are differentially required for endosomal and cell-surface entry of SARS-CoV-2 in lung cell lines.PLoS pathogens · 2024Article
- 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
- Chemoenzymatic Synthesis ofTetrahedron · 2023Article
- Sialosides Containing 7-ACS infectious diseases · 2023Article
- Quantifying Carbohydrate-Active Enzyme Activity with Glycoprotein Substrates Using Electrospray Ionization Mass Spectrometry and Center-of-Mass Monitoring.Analytical chemistry · 2021Article
- Chemoenzymatic Synthesis of Sialosides Containing 7-The Journal of organic chemistry · 2021Article
- Engineering analysis of multienzyme cascade reactions for 3'-sialyllactose synthesis.Biotechnology and bioengineering · 2021Article
- Sialic acid O-acetylation: From biosynthesis to roles in health and disease.The Journal of biological chemistry · 2021Review
- A Chemoenzymatic Synthon Strategy for SynthesizingThe Journal of organic chemistry · 2020Article
- A combined NMR, MD and DFT conformational analysis of 9-O-acetyl sialic acid-containing GM3 ganglioside glycan and its 9-N-acetyl mimic.Glycobiology · 2020Article
- Modified Sialic Acids on Mucus and Erythrocytes Inhibit Influenza A Virus Hemagglutinin and Neuraminidase Functions.Journal of virology · 2020Article
- The role of 9-O-acetylated glycan receptor moieties in the typhoid toxin binding and intoxication.PLoS pathogens · 2020Article
- L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues.Organic & biomolecular chemistry · 2020Article
- Facile chemoenzymatic synthesis of Lewis a (LeCarbohydrate research · 2019Article
- Strategies for chemoenzymatic synthesis of carbohydrates.Carbohydrate research · 2019Review
- Natural and Synthetic Sialylated Glycan Microarrays and Their Applications.Frontiers in molecular biosciences · 2019Review
- A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides.Angewandte Chemie (International ed. in English) · 2018Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
O-Acetylation of sialic acid (Sia) modulates its recognition by sialic acid-binding proteins and plays an important role in biological and pathological processes. 9-O-Acetylation is the most common modification of sialic acid in human. However, study of O-acetylated sialoglycans is hampered due to the instability of O-acetyl group towards pH changes and sensitivity to esterases. Our previous studies demonstrated a chemical biology method to this problem by replacing the oxygen atom in the C9 ester group of sialic acid by a nitrogen to form an amide. Here, we synthesized a library of sixteen new 9-acetamido-9-deoxy-N-acetylneuraminic acid (Neu5Ac9NAc)-containing α2-3- and α2-6-linked sialosides with various underlying glycans using efficient one-pot three-enzyme (OP3E) sialylation systems. Neu5Ac9NAc-containing compounds with a para-nitrophenol aglycon have been used together with their 9-O-acetyl analogs in microtiter plate-based high-throughput substrate specificity studies of nine different sialidases including those from humans and bacteria. In general, similar to 9-O-acetylation, 9-N-acetyl modification of sialic acid in the substrates lowers sialic acid-cleavage activity of most sialidases. In most cases, Neu5Ac9NAc is a good analog of 9-O-acetyl sialic acid. However, exceptions do exist. For example, 9-N- and 9-O-acetyl modifications have different effects on the sialosides cleave efficiencies of a commercially available C. perfringens sialidase as well as recombinant Streptococcus pneumoniae sialidase SpNanC and Bifidobacterium infantis sialidase BiNanH2. The mechanism for the difference awaits further investigation.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.