Controlling Chemical Reactivity with Antibodies

• Published in: Science (American Association for the Advancement of Science) Vol. 260; no. 5106; pp. 337 - 339
• Main Authors: Hsieh, Linda C., Yonkovich, Shirlee, Kochersperger, Lynn, Schultz, Peter G.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Society for the Advancement of Science 16.04.1993; Amer Assoc Advancement Science; American Association for the Advancement of Science; The American Association for the Advancement of Science
• Subjects: 09 BIOMASS FUELS; 090900 - Biomass Fuels- Processing- (1990-); 400201 - Chemical & Physicochemical Properties; 550200 - Biochemistry; Alcohols; ANTIBODIES; Antibodies, Catalytic - chemistry; Antibodies, Monoclonal - chemistry; BASIC BIOLOGICAL SCIENCES; Biological and medical sciences; BIOTECHNOLOGY; Chemical kinetics; CHEMICAL REACTION KINETICS; Chemical reaction, Rate of; CHEMICAL REACTIONS; Chemicals; Chemistry; Chromatography; DENITRIFICATION; Diones; ENZYME ACTIVITY; Esters; Functional groups; Fundamental and applied biological sciences. Psychology; Fundamental immunology; Haptens; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; KETONES; Ketones - chemistry; KINETICS; Molecular immunology; Molecules; Multidisciplinary Sciences; ORGANIC COMPOUNDS; Oxidation-Reduction; Propiophenones - chemistry; PROTEIN ENGINEERING; reaction; REACTION KINETICS; REDUCTION; regulation; Science & Technology; Science & Technology - Other Topics; SELECTIVE CATALYTIC REDUCTION; SPECIFICITY; STEREOCHEMISTRY; Stereoisomerism; stereoselectivity; Techniques; Viral antibodies; MANDELATE; ENANTIOSELECTIVE REDUCTION; ORGANIC-SYNTHESIS; KETONES; Performance evaluation; Chemical reduction; Specificity; Enzymatic activity; Antibody; Enzymatic catalysis; Stereospecificity; Diketone; Chemical synthesis; Alozyme
• ISSN: 0036-8075; 1095-9203
• DOI: 10.1126/science.10049109

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.