ArticleJournal of the American Chemical Society2017
Synthesis of 3-O-Sulfated Oligosaccharides to Understand the Relationship between Structures and Functions of Heparan Sulfate.
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 50 papers.
What it found
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Who cites it
50 citing papers in PubMed, 97 citations in OpenAlex.
- Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides by a Covalent Catch-and-Release Approach.Angewandte Chemie (International ed. in English) · 2026Article
- CRISPR activation screens identify core protein-dependent regulation of heparan sulfate sulfation and ligand specificity.bioRxiv : the preprint server for biology · 2026Article
- Deep Learning-Guided Discovery of Dual Inhibitors of SARS-CoV-2 Entry and 3CL Protease.Molecules (Basel, Switzerland) · 2026Article
- Article
- Synthetic biology for heparin biomanufacturing.Bioresources and bioprocessing · 2026Review
- Controlling the Sulfation Density of Glycosaminoglycan Glycopolymer Mimetics Enables High Antiviral Activity against SARS-CoV-2 and Reduces Anticoagulant Activity.Biomacromolecules · 2025Article
- Recent analytical advances in the detection and characterization of 3-O-sulfated heparan sulfate.Analytical and bioanalytical chemistry · 2025Review
- Involvement of GTPases and vesicle adapter proteins in Heparan sulfate biosynthesis: role of Rab1A, Rab2A and GOLPH3.The FEBS journal · 2025Article
- Expanding the Role of Heparin Derivatives in Oncology: From Anticoagulation to Antitumor Activity.Pharmaceuticals (Basel, Switzerland) · 2025Review
- Sugar-Coated: Can Multivalent Glycoconjugates Improve upon Nature's Design?Journal of the American Chemical Society · 2024Review
- Glycosaminoglycan microarrays for studying glycosaminoglycan-protein systems.Carbohydrate polymers · 2024Review
- Increased 3-Science advances · 2023Article
- Heparan sulfate glycomimeticsChemical science · 2023Article
- Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library.Angewandte Chemie (International ed. in English) · 2023Article
- Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides having a Domain Structure.Angewandte Chemie (International ed. in English) · 2022Article
- Polymers Inspired by Heparin and Heparan Sulfate for Viral Targeting.Macromolecules · 2022Review
- Design and Synthesis of 6-O-Phosphorylated Heparan Sulfate Oligosaccharides to Inhibit Amyloid β Aggregation.Chembiochem : a European journal of chemical biology · 2022Article
- From Steroid and Drug Metabolism to Glycobiology, Using Sulfotransferase Structures to Understand and Tailor Function.Drug metabolism and disposition: the biological fate of chemicals · 2022Review
- Emerging chemical and biochemical tools for studying 3-American journal of physiology. Cell physiology · 2022Review
- Analysis of 3-Analytical chemistry · 2022Article
Corrections and comments
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Authors and funding
10 authors at 4 institutions in 3 countries.
Funding
Abstract
The sulfation at the 3-OH position of glucosamine is an important modification in forming structural domains for heparan sulfate to enable its biological functions. Seven 3-O-sulfotransferase isoforms in the human genome are involved in the biosynthesis of 3-O-sulfated heparan sulfate. As a rare modification present in heparan sulfate, the availability of 3-O-sulfated oligosaccharides is very limited. Here, we report the use of a chemoenzymatic synthetic approach to synthesize six 3-O-sulfated oligosaccharides, including three hexasaccharides and three octasaccharides. The synthesis was achieved by rearranging the enzymatic modification sequence to accommodate the substrate specificity of 3-O-sulfotransferase 3. We studied the impact of 3-O-sulfation on the conformation of the pyranose ring of 2-O-sulfated iduronic acid using NMR, and on the correlation between ring conformation and anticoagulant activity. We identified a novel octasaccharide that interacts with antithrombin and displays anti factor Xa activity. Interestingly, the octasaccharide displays a faster clearance rate than fondaparinux, an FDA-approved pentasaccharide drug, in a rat model, making this octasaccharide a potential short-acting anticoagulant drug candidate that could reduce bleeding risk. Having access to a set of critically important 3-O-sulfated oligosaccharides offers the potential to develop new heparan sulfate-based therapeutics.
Identifiers
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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.