title: Dynamic thiol exchange with β-sulfido-α,β-unsaturated carbonyl compounds and dithianes.
abstract: A reversible covalent bond exchange of thiols, β-sulfido-α,β-unsaturated carbonyls, and dithianes has been studied in DMSO and D(2)O/DMSO mixtures. The equilibrium between thiols and β-sulfido-α,β-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the β-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Gururaj
authors.initials: G
authors.lastname: Joshi
authors.forename: Eric V
authors.initials: EV
authors.lastname: Anslyn
mesh_terms: D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D007659:Ketones; D011807:Quinolizines; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; C438055:dithiane