Large-Scale Preparation of Optically Active Lepidopteran Sex Pheromones Using Bio-Conversion
| Project/Area Number |
15510170
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | National University Corporation Tokyo University of Agriculture and Technology |
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Principal Investigator |
ANDO Tetsu Tokyo University of Agriculture and Technology, Institute of Symbiotic Science and Technology, Professor, 大学院・共生科学技術研究部, 教授 (50151204)
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| Project Period (FY) |
2003 – 2004
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| Project Status |
Completed (Fiscal Year 2004)
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| Budget Amount *help |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥2,300,000 (Direct Cost: ¥2,300,000)
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| Keywords | pheromones / sex pheromones / bio-conversion / epoxy alkenes / optically active epoxides / poly-unsaturated hydrocarbons / chiral pheromones / lepidopteran sex pheromones |
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| Research Abstract |
Lepidopteran sex pheromones have been applied in IPM programs as a monitoring tool and a lure for mass trapping. Furthermore, the disruption of the chemical communication between females and males is possibly carried out by permeating a field with synthetic pheromones. Up to date, chemical structures of the pheromones have been determined for the female moths of more than 500 species. While they are usually composed of primary alcohols and their derivative, many epoxyalkenyl compounds were recently identified from highly evolved insects such as species in the family of Geometridae. Since the epoxy pheromones include chiral centers and it is not easy to prepare them in a large scale only by organic reactions, application of the epoxy pheromones as a mating disruptant is very limited. In order to accomplish a method to synthesize the chiral epoxy compounds easily and abundantly, we tried to find microorganisms which have an ability to introduce a chiral center directly or to produce an appropriate intermediate.
In addition to the epoxy pheromones, which can be derived from linolenic and linolic acids with a homoconjugated polyene system, alkenes and their epoxy derivatives including an extra conjugated polyene system have been identified as a natural pheromone. Therefore, we screened more than 200 imcroorganisms checking abilities for epoxydation, hydroxylation, and desaturatkm around the homocnjugated polyene system of the acids and poly unsaturated hydrocarbons, biosynthetic precursors of epoxy pheromones. As a result, some strains could be successfully selected to study their bioconversion in detailed. We are now examined the optimum incubation condition to confirm the structures of metabolites. Furthermore, novel compounds were detected among the products and we synthesized them using an acelylenic coupling reaction. With the synthetic standards, culture mediums are being reexamining by GC/MS and LC/MS.
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Report
(3 results)
Research Products
(11 results)
