N-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides
| Autor: | Jean-Pierre Vors, Emilie Rouchaud, Stéphanie Norsikian, Lionel Nicolas, Thomas Dröge, Mazen Es-Sayed, Jean-Marie Beau, Margaux Beretta |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), European Academy Bozen/Bolzano (EURAC) |
| Rok vydání: | 2021 |
| Předmět: |
Anomer
Glycosylation Trimethylsilyl Pyrimidine 010405 organic chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Sulfoxide Nucleosides 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Nucleobase 3. Good health carbohydrates (lipids) chemistry.chemical_compound chemistry N-linked glycosylation Azide Physical and Theoretical Chemistry |
| Zdroj: | Organic and Biomolecular Chemistry Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2021, ⟨10.1039/d1ob00493j⟩ |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/d1ob00493j⟩ |
| Popis: | International audience; The synthesis of glycopyranosyl nucleosides modified in the sugar moiety is less frequently explored, notably because of a lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields. |
| Databáze: | OpenAIRE |
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