Synthesis of Cuticular Hydrocarbon Signatures in D. athabasca

Drosophila athabasca, a species complex native to North America, provides a unique opportunity to study nascent speciation arising from sexual selection. Extensive analyses have resulted in complex understandings of CHC involvement in insect mate preference, with minimal work focusing on D. athabasca. Some suggests that these cuticular hydrocarbons (CHCs) potentially act as biochemical signals or pheromones. The goal of this study is to identify, synthesize and measure biologically relevant quantities of CHCs present in this species complex. Compilations of synthetic material will allow for biological evaluation and a greater understanding of CHC function in D. athabasca. Gas chromatography - mass spectrometry (GC-MS) of several isofemale lines from D. athabasca reveals a wide array of functionalities, including: saturated, unsaturated, and branched alkanes, fatty acids, acetates, and esters. Dimethyl disulfide (DMDS) derivatization led to unambiguous determination of the positions of unsaturation. To date, over 100 CHCs have been characterized in D. athabasca using previously described analytical and organic methods. CHC identities were confirmed through comparison to synthetic standards. Monoenes were synthesized by alkylation of alkynes followed by hydrogenation to produce the cis-isomer. Isolated dienes along with other identified CHCs were synthesized using a series of organic and organometallic reactions. An overview of the synthetic routes, along with future directions, will be presented.