Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A
- A convenient and general synthesis of 2-thiocarbohydrates via cerium ammonium nitrate oxidation of the thiocyanate ion is described. Radical addition to glycals proceeds with excellent regio- and good stereoselectivities in only one step, deprotection affords water-soluble 2-thio saccharides. Binding studies to Con A have been performed by isothermal titration calorimetry (ITC) and saturation transfer difference (STD) NMR spectroscopy. The 2-thiomannose derivative binds even stronger to Con A than the natural substrate, offering opportunities for new lectin or enzyme inhibitors.
| Author details: | Prashant Pavashe, Elangovan Elamparuthi, Cornelia Hettrich, Heiko M. Moeller, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1021/acs.joc.6b00987 |
| ISSN: | 0022-3263 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/27518032 |
| Title of parent work (English): | The journal of organic chemistry |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2016 |
| Publication year: | 2016 |
| Release date: | 2020/03/22 |
| Volume: | 81 |
| Number of pages: | 9 |
| First page: | 8595 |
| Last Page: | 8603 |
| Funding institution: | University of Potsdam |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
