A functionalized, deep cavitand catalyzes the aminolysis of a choline derivative.
The aminolysis of choline p-nitrophenyl carbonate is catalyzed with turnover by a deep cavitand bearing an introverted pyridone function. The synergy of action between the recognition of the guest in the binding pocket and the catalytic activity brought to bear by the pyridone is responsible for the high substrate specificity observed.
Gissot
Arnaud
A
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Rebek
Julius
J
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002794:Choline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry*
D000588:Amines; D004952:Esters; D004988:Ethers, Cyclic; D011728:Pyridones; D012118:Resorcinols; C442939:cavitand; D002794:Choline