Biosynthesis of dictyopterene A: stereoselectivity of a lipoxygenase/hydroperoxide lyase from Gomphonema parvulum (Bacillariophyceae)

Abstract

(9S)-Hydroperoxyicosatetraenoic (9S-HPETE) acid is shown to be an intermediate in the biosynthesis of dictyopterene A in the freshwater diatom Gomphonema parvulum; the stereochemistry of (9S)-HPETE and the position of the hydrogen atom at C(16) lost during fatty acid cyclisation and oxidative cleavage of the hydroperoxide were investigated using trapping experiments and chirally deuterium labelled fatty acids.