title: Antibody catalyzed cationic cyclization.
abstract: Two major goals for the design of new catalysts are the facilitation of chemical transformations and control of product outcome. An antibody has been induced that efficiently catalyzes a cationic cyclization in which an acyclic olefinic sulfonate ester substrate is converted almost exclusively (98 percent) to a cyclic alcohol. The key to the catalysis of the reaction and the restriction of the product complexity is the use of antibody binding energy to rigidly enforce a concerted mechanism in accord with the design of the hapten. Thus, the ability to direct binding energy allows the experimenter to dictate a reaction mechanism which is an otherwise difficult task in chemistry. New catalysts for cationic cyclization may be of general use in the formation of carbon-carbon and carbon-heteroatom bonds leading to multi-ring molecules including steroids and heterocyclic compounds.
authors.affiliation: Scripps Research Institute, Department of Molecular Biology, La Jolla, CA 92037.
authors.forename: T
authors.initials: T
authors.lastname: Li
authors.forename: K D
authors.initials: KD
authors.lastname: Janda
authors.forename: J A
authors.initials: JA
authors.lastname: Ashley
authors.forename: R A
authors.initials: RA
authors.lastname: Lerner
mesh_terms: D000818:Animals; D017151:Antibodies, Catalytic / Q000737:chemistry*; D000911:Antibodies, Monoclonal / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D002849:Chromatography, Gas; D003500:Cyclization; D006241:Haptens; D007700:Kinetics; D051379:Mice; D017646:Organosilicon Compounds / Q000737:chemistry*; D013425:Sulfanilic Acids / Q000737:chemistry*
chemical_list: D017151:Antibodies, Catalytic; D000911:Antibodies, Monoclonal; D002412:Cations; D006241:Haptens; D017646:Organosilicon Compounds; D013425:Sulfanilic Acids; C087330:4'-dimethylphenylsilyl-1'-hexen-6'-yl 4-(acetylamino)benzenesulfonate