Design and synthesis of bombykol analogues for probing pheromone-binding protein–ligand interactions

0322756 - ÚOCHB 2009 RIV GB eng J - Journal Article
Mansurova, M. - Klusák, Vojtěch - Nešněrová, P. - Muck, A. - Doubský, J. - Svatoš, Aleš
Design and synthesis of bombykol analogues for probing pheromone-binding protein–ligand interactions.
[Návrh a syntéza analogů bombykolu pro studium interakcí ligandu s proteinem vázajícím feromon (PBP).]
Tetrahedron. Roč. 65, č. 5 (2009), s. 1069-1076. ISSN 0040-4020. E-ISSN 1464-5416
Institutional research plan: CEZ:AV0Z40550506
Keywords : bombykol * pheromone * binding protein * nanoLC
Subject RIV: CC - Organic Chemistry
Impact factor: 3.219, year: 2009

Fluorinated and thioanalogues of Bombyx mori female sex pheromones (bombykol) were designed according to the ab initio calculations. These analogues were synthesized using hydroboration and Sonogashira coupling strategy via (5E,7Z)-undecadien-1-ol as a common intermediate. A new binding assay based on nanoLC-linear ion trap ESI-MS for quantifying complexation of the B. mori pheromone-binding protein (BmPBP) with native and prepared analogues was developed. The dissociation constant (KD) of bombykol and analogue 4 was determined to be 2.1x10−6 M and 2.4x10−6 M, respectively.

Fluorované a thioanalogy bombykolu (samičího sexuálního feromonu bource morušového) byly navrženy na základě ab inicio výpočtů. Tyto analogy byly syntetizovány strategií hydroborace a Sonogashirova couplingu s (5E,7Z)-undekadien-1-olem jakožto běžným meziproduktem. Byl vyvinut test na měření vazebné síly komplexace feromonu či analogu s vazebným proteinem. Naměřené disociační konstanty bombykolu a analogu 4 byly 2.1x10−6 M a 2.4x10−6 M.
Permanent Link: http://hdl.handle.net/11104/0170922