Answers are grounded in this paper and cite their sources.
Mechanistic study reveals that Δ13 desaturation initiates via C13 hydrogen abstraction during moth pheromone biosynthesis, clarifying the enzymatic pathway of double-bond formation.
The synthesis of two hexadeuterated palmitic acids differing in the position of the diagnostic labels, and their use to decipher the cryptoregiochemistry of a Delta13 desaturation are described. A dithiane and a triple bond functionalities were used to introduce the diagnostic (C13 or C14) and tagging (C8 and C9) labels, respectively, in the palmitic acid skeleton. Using these probes, the cryptoregiochemistry of the Delta13 desaturation involved in the biosynthesis of Thaumetopoea pityocampa sex pheromone was studied by means of kinetic isotope effect determinations. Transformation of both (Z)-11-hexadecenoic and 11-hexadecynoic acids into (Z, Z)-11,13-hexadecadienoic and (Z)-13-hexadecen-11-ynoic acids, respectively, is initiated by abstraction of the hydrogen atom at the C13 position, followed by the fast elimination of the C14 hydrogen to give the double bond.
No takes yet. Share an insight, caveat, or question.
Abad et al. (2007) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: