ArticleChemistry (Weinheim an der Bergstrasse, Germany)2011
Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 64 citations in OpenAlex.
- Regio-selective sulfation of heparin mimicking polymers defines in vivo activity.bioRxiv : the preprint server for biology · 2026Article
- Chemical Strategies for Controlling Sulfation in Biomacromolecules.ACS chemical biology · 2026Review
- Fluorosulfate as a Latent Sulfate in Peptides and Proteins.Journal of the American Chemical Society · 2023Article
- A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction.Angewandte Chemie (International ed. in English) · 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
- Modulating Heparanase Activity: Tuning Sulfation Pattern and Glycosidic Linkage of Oligosaccharides.Journal of medicinal chemistry · 2020Article
- Specific Inhibition of Heparanase by a Glycopolymer with Well-Defined Sulfation Pattern Prevents Breast Cancer Metastasis in Mice.ACS applied materials & interfaces · 2019Article
- Programmable one-pot synthesis of heparin pentasaccharides enabling access to regiodefined sulfate derivatives.Chemical science · 2018Article
- Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly.Beilstein journal of organic chemistry · 2017Review
- Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.Carbohydrate research · 2016Article
- Divergent Synthesis of Heparan Sulfate Oligosaccharides.The Journal of organic chemistry · 2015Article
- A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides.Organic & biomolecular chemistry · 2015Article
- Making the longest sugars: a chemical synthesis of heparin-related [4]Chemical science · 2015Article
- Modular synthesis of heparin-related tetra-, hexa- and octasaccharides with differential o-6 protections: programming for regiodefined 6-o-modifications.Molecules (Basel, Switzerland) · 2015Article
- Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.Angewandte Chemie (International ed. in English) · 2014Article
- Tailored design and synthesis of heparan sulfate oligosaccharide analogues using sequential one-pot multienzyme systems.Angewandte Chemie (International ed. in English) · 2013Article
- Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies.Nature communications · 2013Article
- Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1.Angewandte Chemie (International ed. in English) · 2012Article
- Synthesis of disaccharides containing 6-deoxy-α-L-talose as potential heparan sulfate mimetics.Molecules (Basel, Switzerland) · 2012Article
- Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present.Advances in carbohydrate chemistry and biochemistry · 2012Review
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Traditional chemical synthesis of heparin oligosaccharides first involves assembly of the full length oligosaccharide backbone followed by sulfation. Herein, we report an alternative strategy in which the O-sulfate was introduced onto glycosyl building blocks as a trichloroethyl ester prior to assembly of the full length oligosaccharide. This allowed divergent preparation of both sulfated and non-sulfated building blocks from common advanced intermediates. The O-sulfate esters were found to be stable during glycosylation as well as typical synthetic manipulations encountered during heparin oligosaccharide synthesis. Furthermore, the presence of sulfate esters in both glycosyl donors and acceptors did not adversely affect the glycosylation yields, which enabled us to assemble multiple heparin oligosaccharides with preinstalled 6-O-sulfates.
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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.