| Title: | "Synthesis of the deuterated sex pheromone components of the grape borer, Xylotrechus pyrrhoderus" |
| Author(s): | Kiyota R; Yamakawa R; Iwabuchi K; Hoshino K; Ando T; |
| Address: | "Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Tokyo, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 1347-6947 (Electronic) 0916-8451 (Linking) |
| Abstract: | "Adult males of the grape borer, Xylotrechus pyrrhoderus, secrete (S)-2-hydroxy-3-octanone [(S)-1] and (2S,3S)-2,3-octanediol [(2S,3S)-2] from their nota of prothoraces as sex pheromone components. Their structural similarity suggests that one of them is the biosynthetic precursor of the other component. In order to confirm the biochemical conversion, deuterated derivatives of both components were synthesized by starting from a Wittig reaction between hexanal and an ylide derived from D(5)-iodoethane and ending with enantiomeric resolution by chiral HPLC. The molecular ions of 1 and 2 could scarcely be detected by using a GC-MS analysis, and the labeled compounds showed similar mass spectra to the unlabeled pheromone components. However, several fragment ions, including four deuterium atoms, were observed in the mass spectra of their acetate derivatives, indicating that the conversion could be confirmed by examining a compound with the diagnostic ions after acetylation of the volatiles collected from insects treated with the labeled precursors" |
| Keywords: | "Animals Coleoptera/*chemistry/metabolism Deuterium/*chemistry Hydrocarbons, Iodinated/chemistry Male Mass Spectrometry Sex Attractants/biosynthesis/*chemical synthesis/*chemistry Stereoisomerism;" |
| Notes: | "MedlineKiyota, Ryutaro Yamakawa, Rei Iwabuchi, Kikuo Hoshino, Keita Ando, Tetsu eng England 2009/10/08 Biosci Biotechnol Biochem. 2009 Oct; 73(10):2252-6. doi: 10.1271/bbb.90348. Epub 2009 Oct 7" |
