Antibodies gram-scale syntheses

In this respect, reactions catalyzed by monoclonal antibodies have been the focus of much interest [72]. One of the first antibody-supported syntheses on a gram scale and with an enantiomeric excess of up to 99 % was the kinetic resolution of aldol adducts. The products resulting from the retro-aldol reaction served as precursors in the synthesis of epothilones A and B [73]. 

The most active antibody generated, 14D9, elicited to 8a catalyzes the enanti-oselective hydrolysis of the enol ether substrates 10 and 11 to the chiral aldehyde 12 and the enol ether 13 to ketone 14 (Scheme 3) [22,23]. The process is readily scaled up for the cyclic substrate 13 and leads to the ready production of gram quantities of optically active ketone (-)-(S)-14 in 65% yield (based on starting material) and 86% ee, demonstrating the potential of this catalytic antibody in organic synthesis [24]. 

Figure 9.6.16 Example of a gram-scale stereoselective synthesis using a commercial antibody.

---