Abstract
Many moth pheromones are composed of mixtures of acetates of long-chain (≥10 carbon) fatty alcohols. Moth pheromone precursors such as fatty acids and fatty alcohols can be produced in yeast by the heterologous expression of genes involved in insect pheromone production. Acetyltransferases that subsequently catalyze the formation of acetates by transfer of the acetate unit from acetyl-CoA to a fatty alcohol have been postulated in pheromone biosynthesis. However, so far no fatty alcohol acetyltransferases responsible for the production of straight chain alkyl acetate pheromone components in insects have been identified. In search for a non-insect acetyltransferase alternative, we expressed a plant-derived diacylglycerol acetyltransferase (EaDAcT) (EC 2.3.1.20) cloned from the seed of the burning bush (Euonymus alatus) in a yeast system. EaDAcT transformed various fatty alcohol insect pheromone precursors into acetates but we also found high background acetylation activities. Only one enzyme in yeast was shown to be responsible for the majority of that background activity, the acetyltransferase ATF1 (EC 2.3.1.84). We further investigated the usefulness of ATF1 for the conversion of moth pheromone alcohols into acetates in comparison with EaDAcT. Overexpression of ATF1 revealed that it was capable of acetylating these fatty alcohols with chain lengths from 10 to 18 carbons with up to 27- and 10-fold higher in vivo and in vitro efficiency, respectively, compared to EaDAcT. The ATF1 enzyme thus has the potential to serve as the missing enzyme in the reconstruction of the biosynthetic pathway of insect acetate pheromones from precursor fatty acids in yeast.
Highlights
Moth species rely heavily on volatile sex pheromones for mate finding
Fatty alcohols and their corresponding acetates are described by short names, for instance (Z)-11-tetradecen-1-ol is shortened as Z11-14:OH where Z denotes the double bond configuration, 11 the double bond position counting from the carboxylic end, 14 the number of carbons in the chain, and OH denotes the alcohol functional group
Fatty alcohol pheromone components can be synthesized by coexpression of two biosynthetic moth-derived genes in yeast cells [21]
Summary
Moth species rely heavily on volatile sex pheromones for mate finding. More than 600 moth pheromones have been identified and a substantial portion of these contain acetates of fatty alcohols [1]. During the last three decades, pheromone biosynthesis pathways have been studied intensively in many moth species and great progress has been achieved in understanding the biosynthesis of these volatile compounds. The genes coding for the fatty acyl desaturases (FAD) that introduce double bonds into the acyl chain and the fatty acyl reductases (FAR) that convert the fatty acids into fatty alcohols have been characterized [2,3,4,5,6,7,8,9]. The acetylation of fatty alcohols is the last step in the biosynthesis of many moth pheromones. While in vivo labeling experiments have been performed and the substrate specificity
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