ArticleCarbohydrate research2019
A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid.
Article in Carbohydrate research, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- A Biomimetic Self-Adjuvanting Glycoprotein Vaccine Platform Elicits Potent Antitumor Immunity against GD2-Positive Cancers.JACS Au · 2026Article
- Acinetobacter baumannii α2-6-Legionaminyltransferase-Catalyzed Synthesis Reveals Legionaminic Acid Form Selectivity by Antibodies in Pooled Human IgGs.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Broad-Spectrum Legionaminic Acid-Specific Antibodies in Pooled Human IgGs Revealed by Glycan Microarrays with Chemoenzymatically Synthesized Nonulosonosides.Molecules (Basel, Switzerland) · 2024Article
- A bifunctionalOrganic & biomolecular chemistry · 2024Article
- Enabling Chemoenzymatic Strategies and Enzymes for Synthesizing Sialyl Glycans and Sialyl Glycoconjugates.Accounts of chemical research · 2024Article
- Substrate and Process Engineering for Biocatalytic Synthesis and Facile Purification of Human Milk Oligosaccharides.ChemSusChem · 2022Article
- Chemoenzymatic Synthesis of Sialosides Containing 7-The Journal of organic chemistry · 2021Article
- SnClBeilstein journal of organic chemistry · 2019Article
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Authors and funding
6 authors.
Funding
Abstract
A sialyltransferase acceptor tagging and two-step enzymatic reaction strategy has been developed for multigram-scale chemoenzymatic synthesis of 2,7-anhydro-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac), a compound that can serve as a sole carbon source for the growth of Ruminococcus gnavus, a common human gut commensal. Different approaches of introducing hydrophobic UV-active tags to lactose as well-suited sialyltransferase acceptors have been explored and a simple two-step high-yield chemical synthetic procedure has been identified. The UV-active hydrophobic tag facilitates monitoring reaction progress and allows facile product purification by C18-cartridges. A two-step enzyme-catalyzed reaction procedure has been established to combine with C18 cartridge-based purification process for high-yield production of the desired product in multigram scales with the recycled use of chromophore-tagged lactoside starting material and sialoside intermediate. This study demonstrated an environmentally friendly highly-efficient synthetic and purification strategy for the production of 2,7-anhydro-Neu5Ac to explore its potential functions.
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