Controlling chemical reactivity with antibodies.
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.
Department of Chemistry, University of California, Berkeley 94720.
L C
LC
Hsieh
S
S
Yonkovich
L
L
Kochersperger
P G
PG
Schultz
D017151:Antibodies, Catalytic / Q000737:chemistry*; D000911:Antibodies, Monoclonal / Q000737:chemistry; D006241:Haptens; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D011427:Propiophenones / Q000737:chemistry; D013237:Stereoisomerism
D017151:Antibodies, Catalytic; D000911:Antibodies, Monoclonal; D006241:Haptens; D007659:Ketones; D011427:Propiophenones