Spectroscopic investigations of the chiral interactions between lipase and the herbicide dichlorprop

The enantioselective interaction between penicillium expansum alkaline lipase and chiral phenoxypropionic acid herbicide dichlorprop was studied by using UV differential spectrophotometry and fluorescence spectrophotometry in the presence of a pH 8, phosphate buffer solution. Chiral differences in the UV absorption and fluorescence spectra of lipase with dichlorprop were detected. ( R )‐Dichlorprop interacted the strongest with lipase as measured by both UV absorption and fluorescence spectrophotometry, followed by ( Rac )‐dichlorprop, while ( S )‐dichlorprop had the weakest interaction. The hydrophobic interaction seem to play the dominant role in the interactions and the ( R )‐enantiomer needed the minimum put of energy to drive the endothermic reaction, while the Rac ‐type and S ‐type compounds needed more for the reaction to take place. In the meantime, the catalytic hydrolysis of FDA with lipase show that ( R )‐DCPP could inhibit lipase the most strongly relatively at the same condition, perhaps because ( R )‐DCPP had a stronger combining effect and high enantiomeric selectivity on lipase than ( Rac )‐DCPP and ( S )‐DCPP. Chirality, 2009. © 2008 Wiley‐Liss, Inc.