title: Recognition and organocatalysis with a synthetic cavitand receptor.
abstract: The cyclization reaction of an epoxyalcohol is catalyzed by a synthetic cavitand receptor with an inwardly directed carboxylic acid function. The receptor features a hydrophobic pocket in which the substrate is bound and positioned to react in a regioselective manner. The nature of this substrate-catalyst complex and its dynamic properties were investigated by NMR methods and with the aid of a model compound lacking the epoxide function. The kinetic parameters of the cyclization reaction were also studied. A catalytic cycle is proposed and diverse inhibition mechanisms are identified that parallel those encounterd in enzymology.
authors.affiliation: The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Fernando R
authors.initials: FR
authors.lastname: Pinacho Crisóstomo
authors.forename: Agustí
authors.initials: A
authors.lastname: Lledó
authors.forename: Siddhartha R
authors.initials: SR
authors.lastname: Shenoy
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Iwasawa
authors.forename: Julius
authors.initials: J
authors.lastname: Rebek
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds; D004988:Ethers, Cyclic / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D012118:Resorcinols / Q000737:chemistry*
chemical_list: D000438:Alcohols; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand