Abstract
Lipoxygenases convert polyunsaturated fatty acids into a number of chiral hydroperoxides, which are involved in different biological pathways. We applied the exciton-coupled circular dichroism (ECCD) method to determine the absolute configuration of acyclic hydroxylated dienes derived from the lipoxygenase catalyzed dioxygenation of 1(Z),4(Z)-unsaturated fatty acids. The CD spectra of the 2-naphthoate derivatives of reduced hydroperoxides reveal, depending on R or S configuration of the hydroxyl group, a negative or positive chiral twist between the 2-naphthoate chromophore and the diene chromophore in the molecule. Thus, lipoxygenase stereoselectivity can be deduced from a single CD measurement. Chirality 9:563–567, 1997. © 1997 Wiley-Liss, Inc.
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