Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product
| Autor: | Bożena Frąckowiak-Wojtasek, Hubert Wojtasek, Daniel Strub, Weronika Wacławczyk-Biedroń, Magdalena Rzechak |
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| Rok vydání: | 2015 |
| Předmět: |
Colorado
Ketone Clinical Biochemistry Pharmaceutical Science Biochemistry Pheromones chemistry.chemical_compound butanediacetals Drug Discovery Colorado potato beetle Animals Organic chemistry Molecular Biology Glycolic acid Solanum tuberosum chemistry.chemical_classification biology Chemistry Silica gel Organic Chemistry Substrate (chemistry) Stereoisomerism Ketones biology.organism_classification Coleoptera Sex pheromone Molecular Medicine Pheromone Stereoselectivity pheromone inactivation aggregation pheromone |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 25:3560-3563 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2015.06.083 |
| Popis: | Incubation of the Colorado potato beetle aggregation pheromone, (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, with antennal or leg extracts from this beetle gave 6-methyl-5-hepten-2-one as the major product. This ketone was used as a substrate in a stereoselective synthesis of the pheromone. It was attached to the butanediacetal of glycolic acid with good stereoselectivity and the desired isomer was further enriched by purification of the product of this reaction on silica gel. |
| Databáze: | OpenAIRE |
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