Catalysis by a synthetic receptor sealed at one end and functionalized at the other.
A deep cavitand bearing a zinc (II) salen wall catalyzes the hydrolysis of para-nitrophenylcholine carbonate. The closed end of the cavitand properly positions the carbonyl function of the substrate for activation by the metal center. Substrate specificity for acetylcholine derivatives results from simultaneous cation-pi interactions and a C=O- - -Zn coordination bond.
Richeter
Sébastien
S
The Skaggs Institute for Chemical Biology, Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Rebek
Julius
J
D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002794:Choline / Q000031:analogs & derivatives; D004988:Ethers, Cyclic / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009578:Nitrobenzenes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D002254:Carbonates; D004988:Ethers, Cyclic; D009578:Nitrobenzenes; D009942:Organometallic Compounds; D012118:Resorcinols; C442939:cavitand; D015032:Zinc; D002794:Choline