ArticleAngewandte Chemie (International ed. in English)2014
Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 37 citations in OpenAlex.
- Advances in chemoenzymatic synthesis of glycosaminoglycans and proteoglycans.Current opinion in chemical biology · 2026Review
- Iron-catalyzed stereoselective glycosylation for 1,2-cis-aminoglycoside assembly.Nature protocols · 2026Review
- Process Safety Assessment of the Iron-Catalyzed 1,2-Organic process research & development · 2026Article
- Process Safety Assessment of the Iron-Catalyzed 1,2-Research square · 2026Article
- Human Proteoglycan Linkage Region Glycosyltransferases are Dimeric and Show Unexpected Specificities.Angewandte Chemie (International ed. in English) · 2026Article
- Hexafluoroisopropanol-Promoted Stereospecific Glycosylation Enables Efficient Access to N-O-Linked 1,2-JACS Au · 2025Article
- Stereoselective Glycosylation for 1,2-Journal of the American Chemical Society · 2024Article
- Solid-Phase-Supported Chemoenzymatic Synthesis and Analysis of Chondroitin Sulfate Proteoglycan Glycopeptides.Angewandte Chemie (International ed. in English) · 2024Article
- Convergent chemoenzymatic synthesis and biological evaluation of a heparan sulfate proteoglycan syndecan-1 mimetic.Chemical communications (Cambridge, England) · 2021Article
- Long-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions.Organic letters · 2021Article
- Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides.The Journal of organic chemistry · 2020Article
- Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.Chemical science · 2020Article
- Controlled Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides.Angewandte Chemie (International ed. in English) · 2018Article
- Synthesis of Chondroitin Sulfate A Bearing Syndecan-1 Glycopeptide.Organic letters · 2017Article
- Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain.The Journal of organic chemistry · 2016Article
- Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.Carbohydrate research · 2016Article
- Integrated Approach to Identify Heparan Sulfate Ligand Requirements of Robo1.Journal of the American Chemical Society · 2016Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Despite the ubiquitous presence of proteoglycans in mammalian systems, methodologies to synthesize this class of glycopeptides with homogeneous glycans are not well developed. Herein, we report the first synthesis of a glycosaminoglycan family glycopeptide containing two different heparan sulfate chains, namely the extracellular domain of syndecan-3. With the large size and tremendous structural complexity of these molecules, multiple unexpected obstacles were encountered during the synthesis, including high sensitivity to base treatment and the instability of glycopeptides with two glycan chains towards catalytic hydrogenation conditions. A successful strategy was established by constructing the partially deprotected single glycan chain containing glycopeptides first, followed by union of the glycan-bearing fragments and cleavage of the ester-type protecting groups. This work lays the foundation for preparing other members of this important class of molecules.
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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.