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 |
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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 |