THE CANDIDA-ANTARCTICA LIPASE-B CATALYZED KINETIC RESOLUTION OF SEUDENOL IN NONAQUEOUS MEDIA OF CONTROLLED WATER ACTIVITY

For further investigation of the kinetic resolutions in transesterific ation reactions with the highly enantioselective Candida antarctica li pase B, an easy to study model reaction with one typical substrate, th e Douglas Fir Beetle pheromone 3-methyl-2-cyclohexen-1-ol (Seudenol), was developed. The influence of the nature of the solvent and thermody namic water activity was studied. Initial rates showed constant or pro gressively increasing values with increasing water activity. Enantiose lectivity depended on the choice of solvent and descended in most case s with increasing water activity. No general correlations of enantiose lectivity or activity with physicochemical constants of the solvent we re found. However, at a water activity of 0.11 a tendency toward optim um hydrophobicity (i.e log P approximate to 2) for enantioselectivity was observed. Enantiomeric ratios were in the range 8-32.