Antibody catalyzed cationic cyclization

Science. 1994 May 27;264(5163):1289-93. doi: 10.1126/science.8191282.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antibodies, Catalytic / chemistry*
  • Antibodies, Monoclonal / chemistry
  • Catalysis
  • Cations / chemistry*
  • Chromatography, Gas
  • Cyclization
  • Haptens
  • Kinetics
  • Mice
  • Organosilicon Compounds / chemistry*
  • Sulfanilic Acids / chemistry*

Substances

  • Antibodies, Catalytic
  • Antibodies, Monoclonal
  • Cations
  • Haptens
  • Organosilicon Compounds
  • Sulfanilic Acids
  • 4'-dimethylphenylsilyl-1'-hexen-6'-yl 4-(acetylamino)benzenesulfonate