Interaction of l -valinates of biogenic metals with 2-hydroxyethylamines
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Interaction of L-valinates of biogenic metals with 2-hydroxyethylamines* N. S. Kiprova,a Yu. A. Kondratenko,b V. L. Ugolkov,b V. V. Gurzhiy,c T. A. Kochinab aSt.
Petersburg State Institute of Technology, 26 Moscowsky prosp., 190013 St. Petersburg, Russian Federation bI. V. Grebenshchikov Institute of Silicate Chemistry of Russian Academy of Sciences, 2 Makarova nab., 199034 St. Petersburg, Russian Federation. E-mail: [email protected] cInstitute of Earth Sciences, St. Petersburg State University, 7—9 Universitetskaya nab., 199034 St. Petersburg, Russian Federation The interaction of copper(II), zinc(II), nickel(II), and cobalt(II) L-valinates with 2-hydroxyethylamines, viz., triethanolamine, diethanolamine, and tris(hydroxymethyl)aminomethane, was studied for the first time. Formation of new coordination compounds was confirmed using IR and electronic spectroscopies, mass spectrometry, and elemental analysis. The crystal structure of copper(II) L-valinate was determined. The thermal stability and antimicrobial activity data for some prepared complexes of L-valine are also presented. Key words: amino acids, L-valine, triethanolamine, diethanolamine, tris(hydroxymethyl)aminomethane, atranes, biogenic metals, synthesis, structure. L-Valine
((CH3)2CHCH(NH2)COOH) is one of proteinogenic amino acids with branched carbon chains (BCAAs). In contrast to other proteinogenic amino acids, BCAAs (valine, leucine, isoleucine) are not metabolized in the liver. The main catabolism of BCAAs occurs in extrahepatic tissues, mainly in skeletal muscles, for which these amino acids are energy sources.1 In agriculture, L-valine is used as a feed additive along with other amino acids.2,3 The valine, leucine, and isoleucine derivatives are also widely used as biologically active additives and drugs. It is shown that L-valine derivatives possess antibacterial, antimicrobial,4—7 and antitumor8 activity. As known, 2-hydroxyethylamines (HEA) such as triethanolamine (TEA) and diethanolamine (DEA) are parent compounds for synthesis of atranes: silatranes, protatranes, and hydrometallatranes. Atranes possess a wide spectrum of biological activity, including immunomodulatory, adaptogenic, cytotoxic, antitumor, growthstimulating activities, etc.9—11 Hydrometallatranes are usually bi- or tricyclic complexes of hydroxyethylamines with metal salts. Mononuclear cationic, mononuclear mixed-ligand, and polynuclear mixed-ligand complexes of TEA12—18 and DEA19,20 were prepared. All known hydrometallatranes were exclusively prepared by the interaction of 2-hydroxyethylamines with salts of inorganic (SO42–, Cl–, NO3–, ClO4–, etc.) or carboxylic acids * Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9—13, 2019, St. Petersburg, Russia).
(CH3COO–, C6H5CO2–, C4H4O42–, C4O42–, 4-NO2C6H4CO2–, etc.). The interaction of 2-hydroxyethylamines with salts of amino acids was practically not explored. In the present study, copper(II), nickel(II), cobalt(II), and zinc(II) L-valinates were synthesized, and th
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