Asymmetric organic synthesis with catalytic antibodies

Ehud Keinan, Subhash C. Sinha, Doron Shabat, Harel Itzhaky, Jean Louis Reymond

Research output: Contribution to journalReview articlepeer-review

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 α-multistriatin, an important, biologically active natural product can be achieved via antibody catalysis.

Original languageEnglish
Pages (from-to)679-687
Number of pages9
JournalActa Chemica Scandinavica
Volume50
Issue number8
DOIs
StatePublished - Aug 1996
Externally publishedYes

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