ArticleAngewandte Chemie (International ed. in English)2022
Towards a Systematic Understanding of the Influence of Temperature on Glycosylation Reactions.
Article in Angewandte Chemie (International ed. in English), 2022. 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, 47 citations in OpenAlex.
- Industrial Chemical Glycan Synthesis (ICGS): Process Intensification of Glycosylations.Chem & bio engineering · 2026Review
- Automated Syntheses of Xylan Oligosaccharides Containing β3-Linkages Enable Substrate Specificity Studies of Xylanases from Marine Bacteria.Organic letters · 2025Article
- p-nitrobenzyloxycarbonyl protective group as key to automated glycan assembly of neutral human milk oligosaccharides.Nature communications · 2025Article
- Acceptor-Adaptive Automated Glycosylation Optimization for Automated Glycan Assembly.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Automated Glycan Assembly ofJournal of the American Chemical Society · 2025Article
- Carbohydrate Synthesis is Entering the Data-Driven Digital Era.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-The Journal of organic chemistry · 2025Article
- Automated Synthesis of C1-Functionalized Oligosaccharides.Journal of the American Chemical Society · 2025Article
- Approaches to stereoselective 1,1'-glycosylation.Beilstein journal of organic chemistry · 2025Review
- Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate.Organic process research & development · 2024Article
- Automated Synthesis of Algal Fucoidan Oligosaccharides.Journal of the American Chemical Society · 2024Article
- Bimodal Glycosyl Donors as an Emerging Approach Towards a General Glycosylation Strategy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Review
- Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.Organic & biomolecular chemistry · 2024Article
- Glycosaminoglycans: What Remains To Be Deciphered?JACS Au · 2023Review
- VaporSPOT: Parallel Synthesis of Oligosaccharides on Membranes.Journal of the American Chemical Society · 2022Article
- Towards a Systematic Understanding of the Influence of Temperature on Glycosylation Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Recent Advances in Stereoselective ChemicalFrontiers in molecular biosciences · 2022Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Glycosidic bond formation is a continual challenge for practitioners. Aiming to enhance the reproducibility and efficiency of oligosaccharide synthesis, we studied the relationship between glycosyl donor activation and reaction temperature. A novel semi-automated assay revealed diverse responses of members of a panel of thioglycosides to activation at various temperatures. The patterns of protecting groups and the thiol aglycon combine to cause remarkable differences in temperature sensitivity among glycosyl donor building blocks. We introduce the concept of donor activation temperature to capture experimental insights, reasoning that glycosylations performed below this reference temperature evade deleterious side reactions. Activation temperatures enable a simplified temperature treatment and facilitate optimization of glycosyl donor usage. Isothermal glycosylation below the activation temperature halved the equivalents of building block required in comparison to the standard "ramp" regime used in solution- and solid-phase oligosaccharide synthesis to-date.
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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.