Cocaine benzoyl ester

For the cocaine benzoyl ester hydrolysis, the nucleophilic hydroxide ion can approach from the two faces, denoted by Re and Si, of the carbonyl to... 

Fig. 2 Geometries of the transition states optimized at the B3LYP/6-31+G(d) level for the first step of the hydrolysis of CH3COOCH3, (CH3)2CHCOOCH3, C6H5COOCH(CH3)2, the cocaine methyl-ester, and the cocaine benzoyl-ester [63], Internuclear distances are given in angstrom...

For the second step of the cocaine methyl ester hydrolysis involving the water-assisted proton transfer, the calculated energy barrier, 4.8 kcal/mol, associated with transition state TS2dW-Me, is also lower than the corresponding first step. So, with the direct participation of the solvent water molecule in the proton transfer process, the first step of the hydrolysis in aqueous solution should be rate-determining, whether for the cocaine benzoyl ester hydrolysis or for the cocaine methyl ester hydrolysis. This conclusion provides theoretical support for the design of analogs of the first transition state for the cocaine benzoyl ester hydrolysis to elicit anti-cocaine catalytic antibodies [22,25]. 

Fig. 8 Total average number of hydrogen bonds (a) and the corresponding total hydrogen bonding energy (b) between the carbonyl oxygen of cocaine benzoyl ester and the oxyan-ion hole in the simulated the prereactive BChE-cocaine complex (ES), transition states, intermediates, and product for BChE-catalyzed hydrolysis of (-)-cocaine [115]...

Table Summary of the MD-simulated key distances (in A) and the calculated total hydrogen-honding energies (HBE, in kcal/mol) between the oxyanion hole and the carbonyl oxygen of (-)-cocaine benzoyl ester in the first transition state (TSl) [117]...

CHARACTERIZATION OF A HUMAN LIVER COCAINE BENZOYL ESTER HYDROLASE... 

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