title: 2,2,2-Trifluoroethyl 6-thio-β-D-glucopyranoside as a selective tag for cysteines in proteins.
abstract: A synthetic route to a trifluoromethyl and thiol containing glucose derivative (2,2,2-trifluoroethyl 6-thio-β-D-glucopyranoside) is presented, which is based on microwave-assisted Fischer glycosylation under increased pressure. This water-soluble, neutral thiol-compound can be used to selectively introduce a fluorine probe for (19)F NMR spectroscopy on cysteines in proteins. It can be attached under mild conditions in an aqueous environment without the risk of denaturing the protein. This tag has been applied to determine the redox-state of two cysteine residues in a bacterial transcription activator. Qualitative information about the solvent accessibility can be obtained from F-19 solvent PREs.
authors.affiliation: Institute of Chemistry/Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.
authors.forename: Richard F G
authors.initials: RF
authors.lastname: Fröhlich
authors.forename: Evelyne
authors.initials: E
authors.lastname: Schrank
authors.forename: Klaus
authors.initials: K
authors.lastname: Zangger
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011506:Proteins / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C580757:2,2,2-trifluoroethyl 6-thioglucopyranoside; D005960:Glucosides; D011506:Proteins; D013438:Sulfhydryl Compounds; D003545:Cysteine