ArticleJournal of the American Chemical Society2018
Reagent Controlled Stereoselective Synthesis of α-Glucans.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed, 136 citations in OpenAlex.
- Convergent Synthesis of a Bifunctional GPI as a Universal Platform to Access Diverse GPI and GPI-Anchored Protein Probes.Organic letters · 2026Article
- Chemical Synthesis and Immunological Evaluation of Escherichia coli O29, Shigella dysenteriae Serotype 11, and Proteus vulgaris O12 O-Antigen Oligosaccharides.Angewandte Chemie (International ed. in English) · 2026Article
- A chemoproteomic biotechnological toolkit for resolving xylanase specificity in decorated xylan.Nature communications · 2026Article
- Mycobacterium tuberculosis bacteriology and immunity necessitate a multi-pronged immune strategy for vaccination.NPJ vaccines · 2026Review
- Total synthesis of zwitterionic PS A2 oligosaccharides fromScience advances · 2025Article
- Mechanism of 3-The Journal of organic chemistry · 2025Article
- Isothiourea - catalyzed α-selective glycosylations.Chemical communications (Cambridge, England) · 2025Article
- Long, SyntheticJournal of the American Chemical Society · 2025Article
- Collective total synthesis of chartreusin derivatives and bioactivity investigations.Chemical science · 2025Article
- Approaches to stereoselective 1,1'-glycosylation.Beilstein journal of organic chemistry · 2025Review
- A Ligand-Controlled Approach Enabling Gold(I)-Catalyzed Stereoinvertive Glycosylation with Primal GlycosylJournal of the American Chemical Society · 2024Article
- ZnIMolecules (Basel, Switzerland) · 2024Review
- Automated Synthesis of Algal Fucoidan Oligosaccharides.Journal of the American Chemical Society · 2024Article
- Article
- Highly stereoselective α-glycosylation with GalNChemical science · 2024Article
- Recent Progress in 1,2-Molecules (Basel, Switzerland) · 2023Review
- Additive-controlled asymmetric iodocyclization enables enantioselective access to both α- and β-nucleosides.Nature communications · 2023Article
- Semisynthetic Glycoconjugate Vaccine Candidates againstJACS Au · 2022Article
- Synthesis of Fungal Cell Wall Oligosaccharides and Their Ability to Trigger Plant Immune Responses.European journal of organic chemistry · 2022Article
- Beyond GalNAc! Drug delivery systems comprising complex oligosaccharides for targeted use of nucleic acid therapeutics.RSC advances · 2022Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of a glycosylation reaction can vary greatly when switching form one glycosyl donor-acceptor pair to another. We here report a strategy to install cis-glucosidic linkages in a fully stereoselective fashion that is under direct control of the reagents used to activate a single type of donor building block. The activating reagents are tuned to the intrinsic reactivity of the acceptor alcohol to match the reactivity of the glycosylating agent with the reactivity of the incoming nucleophile. A protecting group strategy is introduced that is based on the sole use of benzyl-ether type protecting groups to circumvent changes in reactivity as a result of the protecting groups. For the stereoselective construction of the α-glucosyl linkages to a secondary alcohol, a per-benzylated glusosyl imidate donor is activated with a combination of trimethylsilyltriflate and DMF, while activation of the same imidate donor with trimethylsilyl iodide in the presence of triphenylphosphine oxide allows for the stereoselective cis-glucosylation of primary alcohols. The effectiveness of the strategy is illustrated in the modular synthesis of a Mycobacterium tuberculosis nonasaccharide, composed of an α-(1-4)-oligoglucose backbone bearing different α-glucosyl branches.
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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.