ArticleJournal of the American Chemical Society2009
Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 116 papers.
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Who cites it
116 citing papers in PubMed, 264 citations in OpenAlex.
- Synthetic Heparan Sulfate-like Oligosaccharides as Tools to Decipher Growth Factor Recognition.Journal of medicinal chemistry · 2026Article
- Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides by a Covalent Catch-and-Release Approach.Angewandte Chemie (International ed. in English) · 2026Article
- Merging Enzymatic Catalysis with Iron Catalysis for Highly Stereoselective Heparan Sulfate Oligosaccharide Assembly.Journal of the American Chemical Society · 2026Article
- Synthesis of Heparan Sulfate Hexadecasaccharides and Their Molecular Interaction with Mycobacterial Heparin-Binding Hemagglutinin for the Detection ofJournal of the American Chemical Society · 2026Article
- Chemical Synthesis of Oligosaccharides Derived fromJournal of the American Chemical Society · 2025Article
- Recent analytical advances in the detection and characterization of 3-O-sulfated heparan sulfate.Analytical and bioanalytical chemistry · 2025Review
- Could Hydrophobicity of Sulfated Pseudo-Trisaccharides Derived from Repurposing Aminoglycoside Tobramycin Modulate the Enzymatic Activity of Heparanase?Journal of medicinal chemistry · 2025Article
- Untangling Heparan Sulfate 3-Analytical chemistry · 2025Article
- A Drosophila model of mucopolysaccharidosis IIIB.Genetics · 2025Article
- Glycosaminoglycan microarrays for studying glycosaminoglycan-protein systems.Carbohydrate polymers · 2024Review
- Chemical Synthesis of Δ-4,5 Unsaturated Heparan Sulfate Oligosaccharides for Biomarker Discovery.Organic letters · 2024Article
- Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.Organic & biomolecular chemistry · 2024Article
- Synthetic Heparanase Inhibitors Can Prevent Herpes Simplex Viral Spread.Angewandte Chemie (International ed. in English) · 2023Article
- Rational Design and Expedient Synthesis of Heparan Sulfate Mimetics from Natural Aminoglycosides for Structure and Activity Relationship Studies.Angewandte Chemie (International ed. in English) · 2023Article
- d-Glucuronate and d-Glucuronate Glycal Acceptors for the Scalable Synthesis of d-GlcN-α-1,4-d-GlcA Disaccharides and Modular Assembly of Heparan Sulfate.The Journal of organic chemistry · 2023Article
- Recent Advances in Chemical Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2023Review
- Well-Defined Heparin Mimetics Can Inhibit Binding of the Trimeric Spike of SARS-CoV-2 in a Length-Dependent Manner.JACS Au · 2023Article
- Predicting Structural Motifs of Glycosaminoglycans using Cryogenic Infrared Spectroscopy and Random Forest.Journal of the American Chemical Society · 2023Article
- Heparan sulfate glycomimeticsChemical science · 2023Article
- Sulfation of Heparan and Chondroitin Sulfate Ligands Enables Cell-Specific Homing of Nanoprobes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
56 more citing papers are in PubMed but not listed here.
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
Abstract
Although hundreds of heparan sulfate binding proteins have been identified and implicated in a myriad of physiological and pathological processes, very little information is known about the ligand requirements for binding and mediating biological activities by these proteins. This difficulty results from a lack of technology for establishing structure-activity relationships, which in turn is due to the structural complexity of natural heparan sulfate (HS) and difficulties of preparing well-defined HS oligosaccharides. To address this deficiency, we developed a modular approach for the parallel combinatorial synthesis of HS oligosaccharides that utilizes a relatively small number of selectively protected disaccharide building blocks, which can easily be converted into glycosyl donors and acceptors. The utility of the modular building blocks has been demonstrated by the preparation of a library of 12 oligosaccharides, which has been employed to probe the structural features of HS for inhibiting the protease, BACE-1. The complex variations in activity with structural changes support the view that important functional information is embedded in HS sequences. Furthermore, the most active derivative provides an attractive lead compound for the preparation of more potent compounds, which may find use as a therapeutic agent for Alzheimer's disease.
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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.