ArticleJournal of the American Chemical Society2017
Chemoenzymatic Approach for the Preparation of Asymmetric Bi-, Tri-, and Tetra-Antennary N-Glycans from a Common Precursor.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 84 citations in OpenAlex.
- Revealing the Biological Effect of theJournal of the American Chemical Society · 2026Article
- Chemoenzymatic Synthesis of AsymmetricJournal of the American Chemical Society · 2026Article
- De novo sequencing of glycans by ion mobility-mass spectrometry using a self-expanding database.Nature communications · 2025Article
- Chemical Synthesis of Oligosaccharides Derived fromJournal of the American Chemical Society · 2025Article
- A New Strategy to Functionalize Exosomes via Enzymatic Engineering of Surface Glycans and its Application to Profile Exosomal Glycans and Endocytosis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Expedient Assembly of MultiantennaryJournal of the American Chemical Society · 2025Article
- A Biomimetic Synthetic Strategy Can Provide Keratan Sulfate I and II Oligosaccharides with Diverse Fucosylation and Sulfation Patterns.Journal of the American Chemical Society · 2024Article
- Divergent Enzymatic Assembly of a Comprehensive 64-Membered IgG N-Glycan Library for Functional Glycomics.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Glycoproteomics-Compatible MS/MS-Based Quantification of Glycopeptide Isomers.Analytical chemistry · 2023Article
- Diacetyl strategy for synthesis of NHAc containing glycans: enhancing glycosylation reactivity via diacetyl imide protection.Frontiers in chemistry · 2023Review
- Successive remodeling of IgG glycans using a solid-phase enzymatic platform.Communications biology · 2022Article
- 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
- A new approach for identifying positional isomers of glycans cleaved from monoclonal antibodies.The Analyst · 2021Article
- Recent Advances in the Chemical Biology ofMolecules (Basel, Switzerland) · 2021Review
- Mass spectrometry in clinical glycomics: The path from biomarker identification to clinical implementation.Clinical mass spectrometry (Del Mar, Calif.) · 2020Review
- Recent Progress in Chemo-Enzymatic Methods for the Synthesis of N-Glycans.Frontiers in chemistry · 2020Review
- Cytoplasmic glycoengineering enables biosynthesis of nanoscale glycoprotein assemblies.Nature communications · 2019Article
- Leloir Glycosyltransferases in Applied Biocatalysis: A Multidisciplinary Approach.International journal of molecular sciences · 2019Review
- Review
- Traceless Photolabile Linker Expedites the Chemical Synthesis of Complex Oligosaccharides by Automated Glycan Assembly.Journal of the American Chemical Society · 2019Article
Corrections and comments
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
Progress in glycoscience is hampered by a lack of well-defined complex oligosaccharide standards that are needed to fabricate the next generation of microarrays, to develop analytical protocols to determine exact structures of isolated glycans, and to elucidate pathways of glycan biosynthesis. We describe here a chemoenzymatic methodology that makes it possible, for the first time, to prepare any bi-, tri-, and tetra-antennary asymmetric N-glycan from a single precursor. It is based on the chemical synthesis of a tetra-antennary glycan that has N-acetylglucosamine (GlcNAc), N-acetyllactosamine (LacNAc), and unnatural Galα(1,4)-GlcNAc and Manβ(1,4)-GlcNAc appendages. Mammalian glycosyltransferases recognize only the terminal LacNAc moiety as a substrate, and thus this structure can be uniquely extended. Next, the β-GlcNAc terminating antenna can be converted into LacNAc by galactosylation and can then be enzymatically modified into a complex structure. The unnatural α-Gal and β-Man terminating antennae can sequentially be decaged by an appropriate glycosidase to liberate a terminal β-GlcNAc moiety, which can be converted into LacNAc and then elaborated by a panel of glycosyltransferases. Asymmetric bi- and triantennary glycans could be obtained by removal of a terminal β-GlcNAc moiety by treatment with β-N-acetylglucosaminidase and selective extension of the other arms. The power of the methodology is demonstrated by the preparation of an asymmetric tetra-antennary N-glycan found in human breast carcinoma tissue, which represents the most complex N-glycan ever synthesized. Multistage mass spectrometry of the two isomeric triantennary glycans uncovered unique fragment ions that will facilitate identification of exact structures of glycans in biological samples.
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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.