Synthesis and metabolism of pheromones and pheromone analogues

Thesis/Dissertation · Thu Jan 01 04:00:00 EST 1987

OSTI ID:5174993

Ding, Y S

(9, 10-/sup 3/H/sub 2/)Z9-14:Ac was synthesized at high specific activity (/sup 3/H, 58 Ci/mmole) by partial tritiation of the corresponding alkyne and was converted to the labeled Z9-14:OH and Z9-14:Al to study tissue specificity of acetate esterase (E), alcohol oxidase (OX), and aldehyde dehydrogenase (ALDH) in male and female Heliothis virescens. Soluble and membrane-associated enzyme activities were determined by radio-TLC assays. Compounds of the tritium-labeled Z11-16 series were synthesized and their in vitro fates examined as well. In order to achieve an alternative approach in which (1) pheromone receptor proteins would be stoichiometrically and irreversibly modified, or (2) pheromone-catabolizing enzymes are inactivated by tight-binding or irreversible inhibitors, we have designed analogues of pheromones of lepidopterous insect pests and assayed their biological activity in vitro and in vivo. Various fluorinated molecules such as acyl fluorides, fluoroolefins, 2-fluoro aldehydes, 2,2-difluoro aldehydes and trifluoromethyl ketones were synthesized. The synthesis of some other functional groups such as cyclopropanones, cyclopropanols, cyclopropyl carbinols, cyclopropyl aldehydes and Michael acceptors will also be discussed.

• Research Organization: State Univ. of New York, Stony Brook (USA)
• OSTI ID: 5174993
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
ARTHROPODS
BIOSYNTHESIS
CHROMATOGRAPHY
ENZYME ACTIVITY
ENZYME INHIBITORS
ENZYMES
ESTERASES
HYDROLASES
INSECTS
INVERTEBRATES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
METABOLISM
OXIDOREDUCTASES
PHEROMONE
RADIOASSAY
SECRETION
SEPARATION PROCESSES
SPECIFICITY
STOICHIOMETRY
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TRACER TECHNIQUES
TRITIUM COMPOUNDS