[Molecular characteristics and prediction of the reactive properties of the N-chlorotaurine analogs]

A number of molecular characteristics for the N-chlorotaurine structural analogs, amino acid chloramines and relative compounds have been computed by the ab initio method B3LYP/6-31G. In particular, the characteristics were the Mulliken atomic charges for the chloramine part and its adjacent atoms. A quantitative measure of the capabilities of the chloramines to react with the methionine sulfide group or sulfhydryl group of reduced glutathione was their reaction rate constants. The constants available in literature and determined in own experiments have been depicted with an exponential equation of multiple correlation. In the case of a reaction with methionine, the high determination coefficient (R2) was obtained with five independent variables. They were the charges of active chlorine, nitrogen, carbon bonded with nitrogen, a bond length between nitrogen and carbon atoms, and also molecular mass. The equation has been used to predict the rate constant values for the reaction between compounds that contain active chlorine and methionine. The prediction has showed that structural analogs of N-chlorotaurine bearing two methyl groups at beta-carbon of taurine are remarkable for the low value of the discussed rate constant.