title: Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril.
abstract: The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the CB6-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.
authors.affiliation: Center for Supramolecular Science and Department of Chemistry, University of Miami, Coral Gables, Florida 33124-0431, USA.
authors.forename: Lidia Strimbu
authors.initials: LS
authors.lastname: Berbeci
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Angel E
authors.initials: AE
authors.lastname: Kaifer
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D003538:Cystamine / Q000737:chemistry*; D003543:Cysteamine / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013816:Thermodynamics; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
chemical_list: D001952:Bridged-Ring Compounds; D003538:Cystamine; D003543:Cysteamine; D004220:Disulfides; D007093:Imidazoles; D013438:Sulfhydryl Compounds; C454805:cucurbit(6)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils