ArticleOrganic & biomolecular chemistry2017
Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation.
Article in Organic & biomolecular chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
9 citing papers in PubMed.
- Heparan sulfate and glycomimetics: Advances in synthesis and biological applications for post-stroke neurorepair.Neuroprotection (Chichester, England) · 2026Review
- Synthetic biology for heparin biomanufacturing.Bioresources and bioprocessing · 2026Review
- Heparan sulfate promotes ACE2 super-cluster assembly to enhance SARS-CoV-2-associated syncytium formation.Research square · 2023Article
- Synthesis of selected unnatural sugar nucleotides for biotechnological applications.Critical reviews in biotechnology · 2021Review
- Circulating heparin oligosaccharides rapidly target the hippocampus in sepsis, potentially impacting cognitive functions.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Programmable one-pot synthesis of heparin pentasaccharides enabling access to regiodefined sulfate derivatives.Chemical science · 2018Article
- Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group.Organic letters · 2018Article
- Chemoenzymatic synthesis of heparan sulfate and heparin oligosaccharides and NMR analysis: paving the way to a diverse library for glycobiologists.Chemical science · 2017Article
- Enzymatic Synthesis of Homogeneous Chondroitin Sulfate Oligosaccharides.Angewandte Chemie (International ed. in English) · 2017Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A heparin oligosaccharide having a completely natural structure was successfully synthesized through a chemoenzymatic approach using an unnatural glycosyl acceptor, p-nitrophenyl glucuronide (GlcA-pNP). The use of an inexpensive and commercially available GlcA-pNP acceptor facilitates oligosaccharide recovery and purification on C-18 resin during chemoenzymatic synthesis. Oligosaccharide chain extension and modification afforded a heptasaccharide with gluconic acid residues at its reducing and non-reducing ends. Treatment with periodate oxidation followed by Smith degradation or alkaline elimination resulted in the selective cleavage of vicinal diol-containing glucuronic acid residues affording highly sulfated heparin pentasaccharides having a completely natural structure. This methodology should facilitate the chemoenzymatic synthesis of a family of highly sulfated heparin oligosaccharides with unmodified structures for biological evaluation.
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Registered trials
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