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

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F09%3A00322756" target="_blank" >RIV/61388963:_____/09:00322756 - isvavai.cz</a>

  • Result on the web

  • DOI - Digital Object Identifier

Alternative languages

  • Result language

    angličtina

  • Original language name

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

  • Original language description

    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 andanalogue 4 was determined to be 2.1x106 M and 2.4x106 M, respectively.

  • Czech name

    Návrh a syntéza analogů bombykolu pro studium interakcí ligandu s proteinem vázajícím feromon (PBP)

  • Czech description

    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 2.1x106 M a 2.4x106 M.

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)

Others

  • Publication year

    2009

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Tetrahedron

  • ISSN

    0040-4020

  • e-ISSN

  • Volume of the periodical

    65

  • Issue of the periodical within the volume

    5

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    8

  • Pages from-to

  • UT code for WoS article

    000263218500015

  • EID of the result in the Scopus database