Fluorowany motyw w aktywnych biologicznie peptydomimetykach

• Autorzy: Koroniak-Szejn Katarzyna , Rapp Magdalena

Warianty tytułu

EN

Fluorinated motif in biologically active peptidomimetics

• Języki publikacji: PL

Abstrakty

EN

Incorporation of fluorine atom or fluoroalkyl group into molecules, often induces a remarkable effect upon the physical and chemical properties leading to significant changes of its reactivity [1-5], therefore this modification is often used in the synthesis of drugs and biologically active compounds [6, 7]. The change in reactivity has far-reaching consequences, affects bond energy in the molecule, acidity and alkalinity, hydrogen bond formation and the geometry of the molecule [1-5]. The change in acid-base properties and polarity forced by a fluorine or fluorinated motif in the modified amino acid or peptide molecule has already found numerous applications in bioisosteric mimetics [9]. In addition, using a fluorine atom as a probe, conformation determination and stereochemistry of receptor interaction become more effective due to the possibility of using ¹⁹F NMR spectroscopy. The stereoselective introduction of fluorine atoms can therefore be exploited as a conformational tool for the synthesis of shape-controlled functional molecules. Particular attention has been paid to fluorinated peptidomimetics due to the huge variety of their biological activity. Proteins play a significant role in drug design and synthesis. Peptide binding in living organisms is quite labile which is associated with the presence of proteolytic enzymes. Therefore, to prevent protein hydrolysis, new, modified compounds are thought to mimic the properties and functions of peptide bond. These types of compounds are called peptidomimetics. In this monograph, we will focus on the biologically active fluorinated peptidomimetics, in which the amide bond has been replaced by a fluorinated group and thus they can "mimic" peptide bond functions (pseudopeptides). Other peptidomimetics with typical amide bond, but in which the remaining part of the molecule has been modified by introducing a fluorinated group or fluorine (peptide analogs) will also be discussed. The main goal of this work, however, is to demonstrate the beneficial effect of fluorine on the properties of the modified compounds and associated with it consequences. The superior goal of this work, however, is to demonstrate the unique effect of fluorine on the properties of the target compounds and in the design of higher order structures reflecting a more sophisticated molecular construction that broadens biological mimesis.

Słowa kluczowe

PL

peptydomimetyki; fluoromimetyki; grupa trifluorometylowa; fluor; grupa fluorowinylowa; aktywność biologiczna

EN

peptidomimetics; fluoromimetics; trifluorometyl group; fluorine; fluorovinyl group; biological activity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2020
• Tom: [Z] 74, 3-4
• Strony: 145--179
• Opis fizyczny: Bibliogr. 92 poz., schem.

Twórcy

autor

Koroniak-Szejn Katarzyna

• Wydział Chemii, Uniwersytet im. Adama Mickiewicza w Poznaniu ul. Uniwersytetu Poznańskiego 8, 60-614 Poznań

autor

Rapp Magdalena

• Wydział Chemii, Uniwersytet im. Adama Mickiewicza w Poznaniu ul. Uniwersytetu Poznańskiego 8, 60-614 Poznań

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Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2020).