Controlling Chemical Reactivity with Antibodies
Abstract
The remarkable specificity of an antibody molecule has been used to accomplish highly selective functional group transformations not attainable by current chemical methods. An antibody raised against an amine-oxide hapten catalyzes the reduction of a diketone to a hydroxyketone with greater than 75:1 regioselectivity for one of two nearly equivalent ketone moieties. The antibody-catalyzed reaction is highly stereoselective, affording the hydroxyketone in high enantiomeric excess. Similarly, the reduction of ketones containing branched and aryl substituents, including the highly symmetrical 1-nitrophenyl-3-phenyl-2-propanone, was enantioselective. The simple strategy presented herein may find general applicability to the regio- and stereoselective reduction of a broad range of compounds.
Additional Information
© 1993 American Association for the Advancement of Science. Received 9 December 1992; accepted 26 January 1993. We thank D. Y. Jackson for preparation of the hapten-protein conjugates and J. Stephans and L. Hwang for assistance with purifying the antibodies. Financial support was provided by the Assistant Secretary for Conservation and Renewable Energy and Advanced Industrial Concepts Divisions of the U.S. Department of Energy, under contract DE-AC03-76SF00098. L.C.H. is supported by a National Science Foundation Graduate Fellowship.Additional details
- Eprint ID
- 57656
- Resolver ID
- CaltechAUTHORS:20150519-105415726
- DE-AC03-76SF00098
- Department of Energy (DOE)
- NSF Graduate Fellowship
- Created
-
2015-05-19Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field