Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring. Issue 20 (9th April 2015)

• Record Type: Journal Article
• Authors: Umbreen, Sumaira; Linker, Torsten
• Is Part Of: Chemistry. Volume 21:Issue 20(2015)
• Page Start: 7340
• Page End: 7344
• Publication Date: 2015-04-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201406546
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Conformationally fixed carbohydrate analogues are promising small‐molecule inhibitors for hydrolases like <italic>O</italic>‐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.</p> </abstract>