Controlling chemical reactivity with antibodies

Journal Article · Fri Apr 16 04:00:00 EDT 1993 · Science (Washington, D.C.); (United States)

DOI:https://doi.org/10.1126/science.10049109· OSTI ID:6389744

Hsieh, L C; Schultz, P G ^[1]; Yonkovich, S; Kochersperger, L ^[2]

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1. Univ. of California, Berkeley (United States)
2. Affymax Research Inst., Palo Alto, CA (United States)

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. 18 refs., 2 figs., 1 tab.

• DOE Contract Number: AC03-76SF00098
• OSTI ID: 6389744
• Journal Information: Science (Washington, D.C.); (United States), Journal Name: Science (Washington, D.C.); (United States) Vol. 260:5106; ISSN SCIEAS; ISSN 0036-8075
• Country of Publication: United States
• Language: English

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59 BASIC BIOLOGICAL SCIENCES
ANTIBODIES
BIOTECHNOLOGY
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DENITRIFICATION
ENZYME ACTIVITY
KETONES
KINETICS
ORGANIC COMPOUNDS
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REACTION KINETICS
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SELECTIVE CATALYTIC REDUCTION
SPECIFICITY
STEREOCHEMISTRY