ENANTIOSELECTIVITY VS. KINETIC RESOLUTION IN ANTIBODY CATALYSIS - FORMATION OF THE (S)-PRODUCT DESPITE PREFERENTIAL BINDING OF THE (R)-INTERMEDIATE

Antibody 14D9, which catalyzes the stereoselective transformation of a chiral enol ethers into the corresponding (S)-ketals, resolves a racem ic mixture of structurally similar chiral enol ethers by selective con version of the (R)-enol ether into the (R)-ketal, raising the possibil ity that the (S) transition state is preferencially stabilized by the antibody despite a better binding of the (R) intermediate.