Thioethyl-, Vinyl-, Ethyl Octanoate Esters and Octanoic Acid as Acyl Donors in Lipase Catalysed Acyl Transfer Reactions

S-Ethyl thiooctanoate, vinyl octanoate, ethyl octanoate and octanoic acid were studied as acyl donors in a lipase catalysed acyl transfer reaction with 2-octanol as acyl acceptor. The reaction conditions had a pronounced effect on the equilibrium displacement and the apparent enantioselectivity. The thioethyl and vinyl esters proved to be efficient acyl donors under atmospheric pressure and 39 d`C, affording a high apparent enantiomeric ratio. Under these reaction conditions the apparent enantioselectivity seemed to be enhanced by water, which was present in the reaction system and caused the production of octanoic acid, by hydrolysis of me acyl enzyme.