ArticleJournal of the American Chemical Society2016
Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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Who cites it
25 citing papers in PubMed, 86 citations in OpenAlex.
- A Protecting-Group-Free S‑Glycosylation Strategy for Complex S‑Glycopeptide Synthesis.JACS Au · 2026Article
- Using Synthetic Glycans to Investigate Anti-Glycan Antibodies and Explore Their Medical Potential.Angewandte Chemie (International ed. in English) · 2026Review
- Article
- Synthesis and Structural Confirmation of Secalosides A and B.Journal of the American Chemical Society · 2026Article
- Article
- Exploration of the Transglycosylation Activity of Barley Limit Dextrinase for Production of Novel Glycoconjugates.Molecules (Basel, Switzerland) · 2023Article
- Site-Selective Modification of (Oligo)Saccharides.ACS catalysis · 2022Review
- Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor.The Journal of organic chemistry · 2022Article
- Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.Chemical reviews · 2022Review
- Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-Chemical science · 2022Article
- Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars.ChemSusChem · 2022Article
- Protecting-group-freeGreen chemistry : an international journal and green chemistry resource : GC · 2021Article
- A Palette of Minimally Tagged Sucrose Analogues for Real-Time Raman Imaging of Intracellular Plant Metabolism.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- A Palette of Minimally Tagged Sucrose Analogues for Real-Time Raman Imaging of Intracellular Plant Metabolism.Angewandte Chemie (International ed. in English) · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- Metal-free glycosylation with glycosyl fluorides in liquid SOBeilstein journal of organic chemistry · 2021Article
- Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride.Organic letters · 2021Article
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
- Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids.Nature communications · 2018Article
- Hitting the sweet spot.Nature chemistry · 2018Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3'-position or 1'-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.
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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.