ArticleChemistry (Weinheim an der Bergstrasse, Germany)2008
Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Revealing the Biological Effect of theJournal of the American Chemical Society · 2026Article
- Synthetic O-Polysaccharide Backbone Units for a Single Antigen Vaccine Against Two Major Non-Typhoidal Salmonella Serovars.Angewandte Chemie (International ed. in English) · 2026Article
- Stereoselective Synthesis of Sialyl LewisAngewandte Chemie (International ed. in English) · 2023Article
- Divergent Enzymatic Assembly of a Comprehensive 64-Membered IgG N-Glycan Library for Functional Glycomics.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Chemoenzymatic Synthesis of Complex N-Glycans of the Parasite S. mansoni to Examine the Importance of Epitope Presentation on DC-SIGN recognition.Angewandte Chemie (International ed. in English) · 2021Article
- Article
- Unique Binding Specificities of Proteins toward Isomeric Asparagine-Linked Glycans.Cell chemical biology · 2019Article
- Synthetic standard aided quantification and structural characterization of amyloid-beta glycopeptides enriched from cerebrospinal fluid of Alzheimer's disease patients.Scientific reports · 2019Article
- Streamlining the chemoenzymatic synthesis of complex N-glycans by a stop and go strategy.Nature chemistry · 2019Article
- Chemoenzymatic Synthesis of Asymmetrical Multi-Antennary N-Glycans to Dissect Glycan-Mediated Interactions between Human Sperm and Oocytes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Designer α1,6-Fucosidase Mutants Enable Direct Core Fucosylation of Intact N-Glycopeptides and N-Glycoproteins.Journal of the American Chemical Society · 2017Article
- Chemoenzymatic Approach for the Preparation of Asymmetric Bi-, Tri-, and Tetra-Antennary N-Glycans from a Common Precursor.Journal of the American Chemical Society · 2017Article
- Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly.Beilstein journal of organic chemistry · 2017Review
- Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Chemical Synthesis of the Repeating Unit of Type V Group B Streptococcus Capsular Polysaccharide.Organic letters · 2016Article
- Substrate specificity of FUT8 and chemoenzymatic synthesis of core-fucosylated asymmetric N-glycans.Organic & biomolecular chemistry · 2016Article
- Endo-F3 Glycosynthase Mutants Enable Chemoenzymatic Synthesis of Core-fucosylated Triantennary Complex Type Glycopeptides and Glycoproteins.The Journal of biological chemistry · 2016Article
- Chemical Synthesis of GM2 Glycans, Bioconjugation with Bacteriophage Qβ, and the Induction of Anticancer Antibodies.Chembiochem : a European journal of chemical biology · 2016Article
- Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.Chemistry & biology · 2014Review
- In situ preactivation strategies for the expeditious synthesis of oligosaccharides: A review.Journal of carbohydrate chemistry · 2014Article
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3 authors.
Funding
Abstract
Synthesis of N-glycans is of high current interests due to their important biological properties. A highly efficient convergent strategy based on the pre-activation method for assembly of the complex type core fucosylated bi-antennary N-glycan dodecasaccharide has been developed. Retrosynthetically, this extremely challenging target is broken down to three modules: a sialyl disaccharide, a glucosamine building block and a hexasaccharide diol acceptor. The sialyl disaccharide was easily obtained by selective activation of a new 5-N-trichloroacetyl protected sialyl donor in the presence of a thiogalactoside acceptor. The hexasaccharide diol module was produced by double mannosylation of a fucosylated tetrasaccharide acceptor, which in turn was generated by glycosylation of a alpha-fucosylated disaccharide with a beta-mannose containing disaccharide donor. The union of the three modules was performed in one-pot giving the fully protected dodecasaccharide in high yield. This synthesis is characterized by minimum protective group and aglycon adjustment on oligosaccharide intermediates, thus greatly enhancing the overall synthetic efficiency. The modular feature of this strategy suggests that this method can be readily adapted to the synthesis of a wide variety of N-glycan structures.
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