Catalytic antibodies acyl transfer

Clearly, the oxyanion hole is now as significant a feature of the binding site of such acyl transfer abzymes as it is already for esterases and peptidases — and not without good reason. Knossow has analysed the structures of three esterase-like catalytic antibodies, each elicited in response to the same phosphonate TSA hapten (Charbonnier et al., 1997). Catalysis for all three is accounted for by transition state stabilization and in each case there is an... 

A stable chemical analog that mimics the transition state of a chemical reaction was the first approach used to elicit catalytic antibodies (Fig. 4) (3-5). Acyl transfer reactions are the most studied type of catalytic antibody reaction, and a wealth of knowledge about this reaction has been garnered through... 

Janda KD, Weinhouse Ml, Schloeder DM, Lemer RA, Benkovic SJ. Bait and switch strategy for obtaining catalytic antibodies 68. with acyl-transfer capabilities. J. Am. Chem. Soc. 1990 112(3) 1274-1275. 

Catalytic antibodies have been produced to catalyze an impressive variety of chemical reactions. For instance, stable phosphonic esters (or lactones, respectively) have been used as transition state mimics for the hydrolysis of esters and amides [555-557], acyl transfer [558] and lactonization [559] reactions, which all proceed via a tetrahedral carbanionic intermediate. In some instances, the reactions proved to be enantiospecific [560]. Elimination reactions [561, 562], reductions [563], formation and breakage of C-C bonds [564,565] and even photochemical reactions [566] can be catalyzed. The cleavage of an ether [567] and cis-trans isomerization of alkenes have been reported [568]. 

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