ArticleChemical science2018
Chemoenzymatic synthesis of glycopeptides bearing rare N-glycan sequences with or without bisecting GlcNAc.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 21 citations in OpenAlex.
- Chemoenzymatic Synthesis of Asymmetric Bisecting Bi-, Tri-, and Tetra-AntennaryJournal of the American Chemical Society · 2025Article
- Divergent Enzymatic Assembly of a Comprehensive 64-Membered IgG N-Glycan Library for Functional Glycomics.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Stereoselective synthesis of photoactivatable Man(β1,4)GlcNAc-based bioorthogonal probes.Tetrahedron letters · 2023Article
- Profiling the Bisecting N-acetylglucosamine Modification in Amniotic Membrane via Mass Spectrometry.Genomics, proteomics & bioinformatics · 2022Article
- Systematic synthesis of bisectedChemical science · 2022Article
- Recent Chemical and Chemoenzymatic Strategies to Complex-TypeFrontiers in chemistry · 2022Review
- The Essential Functions and Detection of Bisecting GlcNAc in Cell Biology.Frontiers in chemistry · 2020Review
- Review
Corrections and comments
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Authors and funding
10 authors at 4 institutions in 2 countries.
Funding
Abstract
N-Linked glycopeptides have highly diverse structures in nature. Herein, we describe the first synthesis of rare multi-antennary N-glycan bearing glycan chains on 6-OH of both α1,6- and α1,3-linked mannose arms. To expedite divergent generation of N-glycan structures, four orthogonal protective groups were installed at the branching points on the core tetrasaccharide, which could be removed individually without affecting one another. In addition, the synthetic route is flexible, allowing a bisecting glucosamine moiety to be introduced at a late stage of the synthesis, further expanding the diversity of sequences that could be achieved. The bisecting glucosamine unit significantly reduced the glycosylation yields of adjacent mannoses, which was attributed to steric hindrance imposed by the glucosamine based on molecular modelling analysis. The N-glycans were then transformed to oxazoline donors and ligated with a glycopeptide acceptor from haptoglobin promoted by the wild type
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Registered trials
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