Sex pheromone biosynthesis in Mamestra brassicae l. (lepidoptera: noctuidae); stereochemistry of the Δ11 desaturation

Abstract

(11S, 12R)-and (11R, 12S)-[²H₁₄]palmitic acids 1 are converted in the pheromone gland of the moth Mamestra brassicae into the [²H₁₁]- or [²H₁₃]-hexadec-11-enyl acetates 2 by a formal syn-elimination of the C(11)-H_R and C(12)-H_R hydrogen atoms; this characterises the unique Δ¹¹ desaturase from insects as closely related to the Δ⁹ desaturases from mammals, plants and bacteria.