| Title: | Asymmetric organic synthesis with catalytic antibodies |
| Author(s): | Keinan E; Sinha SC; Shabat D; Itzhaky H; Reymond JL; |
| Address: | "Scripps Research Institute, La Jolla, CA 92037, USA" |
| DOI: | 10.3891/acta.chem.scand.50-0679 |
| ISSN/ISBN: | 0904-213X (Print) 0904-213X (Linking) |
| Abstract: | "The science of catalytic antibodies has undergone a rapid maturation process within its first nine years of existence. From initial 'proof of concept' and demonstration of fundamental, enzyme-like characteristics, antibodies have been shown to catalyze a remarkably broad scope of organic transformations, including difficult and unfavorable chemical reactions. Yet, the ultimate testing ground for new concepts in organic chemistry has always been the synthesis of natural products. Here we focus on several issues related to the applicability of antibody catalysis in organic synthesis. We show that (a) in the hydrophobic environment of the antibody active site, short-lived intermediates can be formed and reacted in a controlled way, thus allowing antibodies to catalyze reactions that are normally incompatible with aqueous media, (b) the intrinsic order of reactivity (chemoselectivity) in a series of structurally related enol ethers and ketals can be inverted from 1:10 in the uncatalyzed hydrolysis reaction to 1000:1 under antibody catalysis, and (c) an efficient total synthesis of alpha-multistriatin, an important, biologically active natural product can be achieved via antibody catalysis" |
| Keywords: | "Antibodies, Catalytic/*metabolism Binding Sites Dioxolanes/*chemical synthesis Hydrogen-Ion Concentration Hydrolysis Kinetics Models, Chemical Molecular Structure Pheromones/*chemical synthesis Water;" |
| Notes: | "MedlineKeinan, E Sinha, S C Shabat, D Itzhaky, H Reymond, J L eng GM47993/GM/NIGMS NIH HHS/ GM49736/GM/NIGMS NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. Research Support, U.S. Gov't, P.H.S. Denmark 1996/08/01 Acta Chem Scand (Cph). 1996 Aug; 50(8):679-87. doi: 10.3891/acta.chem.scand.50-0679" |
