Hydrogen bonding and protonation effects in amino acids' anthraquinone derivatives - spectroscopic and electrochemical studies

Sandra Ramotowska , Dorota Zarzeczańska , Iwona Dąbkowska , Anna Wcisło , Paweł Niedziałkowski , Elżbieta Czaczyk , Beata Grobelna , Tadeusz Ossowski

Abstract

Six novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical properties are discussed in this work. In studied compounds, selected amino acid residues (L-Aspartic acid, LGlutamic acid, L-Glutamine, L-Histidine, L-Lysine, L-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atomof the piperazine ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry, 1HNMR, UV–Vis, IR spectroscopy), acid-base (electrochemical and UV–Vis) titrations, and cyclic voltammetry methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structureproperties links were established. They are indicative of the specific interactions within and/or in-between amino acid side groups,which are prone to formboth, intra- and intermolecular hydrogen bonds aswell as electrostatic interactions with the anthraquinone system.
Author Sandra Ramotowska (FCh / KChBionieorg. / LII)
Sandra Ramotowska ,,
- Laboratory of Intermolecular Interactions
, Dorota Zarzeczańska (FCh / DACh / LSCh)
Dorota Zarzeczańska,,
- Laboratory of Supramolecular Chemistry
, Iwona Dąbkowska (FCh / DACh / LSCh)
Iwona Dąbkowska,,
- Laboratory of Supramolecular Chemistry
, Anna Wcisło (FCh / DACh / LSCh)
Anna Wcisło,,
- Laboratory of Supramolecular Chemistry
, Paweł Niedziałkowski (FCh / DACh / LSCh)
Paweł Niedziałkowski,,
- Laboratory of Supramolecular Chemistry
, Elżbieta Czaczyk (FCh / DACh / LSCh)
Elżbieta Czaczyk ,,
- Laboratory of Supramolecular Chemistry
, Beata Grobelna (FCh / DACh / LChAC)
Beata Grobelna,,
- Laboratory of chemistry and Analytics of Cosmetics
, Tadeusz Ossowski (FCh / DACh / LSCh)
Tadeusz Ossowski,,
- Laboratory of Supramolecular Chemistry
Journal seriesSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, ISSN 1386-1425, (A 30 pkt)
Issue year2019
Vol222
Pages1-11
Publication size in sheets0.5
Article number117226
Keywords in EnglishAnthraquinone, amino acids, pyroglutamic acid, hydrogen bonding, protonation, electrochemistry
ASJC Classification1607 Spectroscopy; 3105 Instrumentation; 3107 Atomic and Molecular Physics, and Optics; 1602 Analytical Chemistry
DOIDOI:10.1016/j.saa.2019.117226
URL https://doi.org/10.1016/j.saa.2019.117226
Languageen angielski
Score (nominal)30
ScoreMinisterial score = 30.0, 13-09-2019, ArticleFromJournal
Publication indicators WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 1.104; WoS Impact Factor: 2017 = 2.88 (2) - 2017=2.571 (5)
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