Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
| Autor: | Marloes Bakker, Gijsbert A. van der Marel, Stefan van der Vorm, Jeroen D. C. Codée, Herman S. Overkleeft, Jacob M. A. van Hengst |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Glycosylation
animal structures Stereochemistry Stereoisomerism macromolecular substances 010402 general chemistry stereoselectivity 01 natural sciences Catalysis chemistry.chemical_compound enzyme mechanisms Nucleophile Glycosyl Reactivity (chemistry) Glycosides Glycosyl donor Chemistry 010405 organic chemistry Communication Glycosyl acceptor Galactose Benzene General Chemistry General Medicine Communications 0104 chemical sciences carbohydrates (lipids) Nitrobenzoates reactivity tuning acceptor reactivity Stereoselectivity lipids (amino acids peptides and proteins) |
| Zdroj: | Angewandte Chemie (International Ed. in English) Angewandte Chemie International Edition, 57(27), 8240-8244 Angewandte Chemie International Edition |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting‐group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis‐glucosylations. |
| Databáze: | OpenAIRE |
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