Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring
- 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.
| Author details: | Sumaira Umbreen, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1002/chem.201406546 |
| ISSN: | 0947-6539 |
| ISSN: | 1521-3765 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/25858360 |
| Title of parent work (English): | Chemistry - a European journal |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2015 |
| Publication year: | 2015 |
| Release date: | 2017/03/27 |
| Tag: | carbohydrates; cycloaddition; enzyme inhibitors; rearrangement; selective syntheses |
| Volume: | 21 |
| Issue: | 20 |
| Number of pages: | 5 |
| First page: | 7340 |
| Last Page: | 7344 |
| Funding institution: | University of Potsdam |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
