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J Chem Ecol

Title:		"Design and Synthesis of Fluorophore-Tagged Disparlure Enantiomers to Study Pheromone Enantiomer Discrimination in the Pheromone-Binding Proteins from the Gypsy Moth, Lymantria dispar"
Author(s):		Pinnelli GR; Plettner E;
Address:		"Department of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6, Canada. Department of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6, Canada. plettner@sfu.ca"
Journal Title:		J Chem Ecol
Year:		2022
Volume:		20211011
Issue:		3
Page Number:		312 - 322
DOI:		10.1007/s10886-021-01318-2
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Fluorescent analogues of the gypsy moth sex pheromone (+)-disparlure (1) and its enantiomer (-)-disparlure (ent-1) were designed, synthesized, and characterized. The fluorescently labelled analogues 6-FAM (+)-disparlure and 1a 6-FAM (-)-disparlure ent-1a were prepared by copper-catalyzed azide-alkyne cycloaddition of disparlure alkyne and 6-FAM azide. These fluorescent disparlure analogues 1a and ent-1a were used to measure disparlure binding to two pheromone-binding proteins from the gypsy moth, LdisPBP1 and LdisPBP2. The fluorescence binding assay showed that LdisPBP1 has a stronger affinity for 6-FAM (-)-disparlure ent-1a, whereas LdisPBP2 has a stronger affinity for 6-FAM (+)-disparlure 1a, consistent with findings from previous studies with disparlure enantiomers. The 6-FAM disparlure enantiomers appeared to be much stronger ligands for LdisPBPs, with binding constants (K(d)) in the nanomolar range, compared to the fluorescent reporter 1-NPN (which had K(d) values in the micromolar range). Fluorescence competitive binding assays were used to determine the displacement constant (K(i)) for the disparlure enantiomers in competition with fluorescent disparlure analogues binding to LdisPBP1 and LdisPBP2. The K(i) data show that disparlure enantiomers can effectively displace the fluorescent disparlure from the binding pocket of LdisPBPs and, therefore, occupy the same binding site"
Keywords:		Alkanes Animals Carrier Proteins/chemistry/metabolism *Moths/chemistry Pheromones/metabolism *Sex Attractants/chemistry Cis-epoxide Click reaction Enantioselective synthesis Fluorescein Fluorescence binding assays Fluorophore-tagged disparlure enantiomers;
Notes:		"MedlinePinnelli, Govardhana R Plettner, Erika eng 06088/nserc discovery/ 477793/nserc discovery accelerator award/ 2021/10/12 J Chem Ecol. 2022 Mar; 48(3):312-322. doi: 10.1007/s10886-021-01318-2. Epub 2021 Oct 11"