Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring
| Autor: | Torsten Linker, Sumaira Umbreen |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Glucosamine
Molecular Structure Biochemical Phenomena Chemistry Stereochemistry Organic Chemistry Carbohydrates Molecular Conformation Stereoisomerism General Chemistry Carbohydrate Disaccharides Ring (chemistry) beta-N-Acetylhexosaminidases Catalysis Cycloaddition Beckmann rearrangement Institut für Chemie Stereoselectivity Glycosamine |
| Popis: | Conformationally fixed carbohydrate analogues are promising small-molecule inhibitors for hydrolases like O-GlcNAcase (OGA); however, their synthesis usually requires many steps. Herein we describe cycloadditions of dichloroketene to various glycals and subsequent Beckmann rearrangements, which offer an easy and stereoselective entry to glycosamine derivatives in good yields. The reactions are applicable for hexoses, pentoses, and disaccharides, and transformations to the corresponding imidates proceed smoothly. First biological tests reveal that such imidates indeed inhibit human OGA. |
| Databáze: | OpenAIRE |
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