Antibody catalyzed cationic cyclization.
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.
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Scripps Research Institute, Department of Molecular Biology, La Jolla, CA 92037.
Janda
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Ashley
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Lerner
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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*
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