Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril.
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.
Berbeci
Lidia Strimbu
LS
Center for Supramolecular Science and Department of Chemistry, University of Miami, Coral Gables, Florida 33124-0431, USA.
Wang
Wei
W
Kaifer
Angel E
AE
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
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