Exciton-coupled circular dichroism (ECCD) in acyclic hydroxylated dienes: A sensitive method for the direct stereochemical assignment of lipoxygenase products
✍ Scribed by Claus Schneider; Peter Schreier; Hans-Ulrich Humpf
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 95 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0899-0042
No coin nor oath required. For personal study only.
✦ Synopsis
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.