6533b82dfe1ef96bd1290895

RESEARCH PRODUCT

Theozyme for antibody aldolases. Characterization of the transition-state analogueElectronic supplementary information (ESI) available: MP2/6-31G** energies, imaginary frequencies and cartesian coordinates. See http://www.rsc.org/suppdata/ob/b2/b209636f/

subject

description

A theozyme for antibody aldolases has been studied at the MP2/6-31G** computational level. Formation of two cooperative hydrogen-bonds between the acidic hydrogen atoms of the enamine and of a methanol molecule with the oxygen atom of the aldol acceptor markedly favors the C–C bond-formation associated with the aldol reaction. A comparative analysis of the geometry, the charge distribution and the shape of the molecular electrostatic potential of the transition structure (TS) with the covalent adduct, resulting from the reaction of methylamine and the β-diketone used as a hapten allows us to characterize the transition-state analogue (TSA) generated at immunization. This finding allows us to propose a hapten based on a chiral β-ketosulfoxide that could give the formation of a TSA that addresses the tetrahedral geometry of the TS.