title: Metabolically blocked analogs of housefly sex pheromone: II. Metabolism studies.
abstract: Analogs of (Z)-9-tricosene (Z9-23: Hy) bearing methyl substituents, cyclopropyl groups, fluorine substituents, and additional double bonds were used to probe the substrate requirements for the monooxygenase system that converts Z9-23: Hy to the corresponding epoxide and ketone. Three of the seven analogs tested, 10-fluoro-(Z)-14-tricosene, 10,10-difluoro-(Z)-14-tricosene, and 14-methyl-(Z)-9-tricosene, were metabolized to the corresponding epoxide. Compounds with two methyl groups, a cyclopropane group, a hydroxy group, or an additional double bond at the 14 position were not epoxidized at the 9,10 position. This suggests that only minimal structural change at the 14-position of Z9-23: Hy is allowed with retention of metabolic activity. None of the analogs tested were hydroxylated at the position equivalent to the 14 position of Z9-23:Hy. Of the 13 analogs tested as inhibitors of Z9-23:Hy metabolism, the two compounds that were the most effective inhibitors in both male and female houseflies were (Z)-14-tricosen-10-one and 1-nonyl-1-[(Z)-4-tetradecen-1-yl]-cyclopropane. These data show that the poly substrate monooxy genase that metabolizes Z9-23: Hy in the housefly has very strict structural requirements for the substrate.
authors.affiliation: Department of Biochemistry, University of Nevada, 89557-0014, Reno, Nevada.
authors.forename: L
authors.initials: L
authors.lastname: Guo
authors.forename: B
authors.initials: B
authors.lastname: Latli
authors.forename: G D
authors.initials: GD
authors.lastname: Prestwich
authors.forename: G J
authors.initials: GJ
authors.lastname: Blomquist