Application of spectroscopic methods (FT-IR, Raman, ECD and NMR) in studies of identification and optical purity of radezolid
PBN-AR
Instytucja
Instytut Fizyki Molekularnej Polskiej Akademii Nauk
Informacje podstawowe
Główny język publikacji
en
Czasopismo
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (30pkt w roku publikacji)
ISSN
1386-1425
EISSN
Wydawca
PERGAMON-ELSEVIER SCIENCE LTD
DOI
URL
Rok publikacji
2017
Numer zeszytu
Strony od-do
116-122
Numer tomu
183
Link do pełnego tekstu
Identyfikator DOI
Liczba arkuszy
Autorzy
(liczba autorów: 7)
Pozostali autorzy
+ 6
Słowa kluczowe
en
Radezolid
FT-IR
Raman
NMR
ECD
Theoretical approach
Streszczenia
Język
en
Treść
In the presented study, N-[(5S)-3-(2-fluoro-4'-[(1H-1,2,3-triazol-5-ylmethyl)amino]methylbiphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methylacetamide (radezolid) was synthesized and characterized using FT-IR, Raman, ECD and NMR. The aim of this work was to assess the possibility of applying classical spectral methods such as FT-IR, Raman, ECD and NMR spectroscopy for studies on the identification and optical purity of radezolid. The experimental interpretation of FT-IR and Raman spectra of radezolid was conducted in combination with theoretical studies. Density functional theory (DFT) with the B3LYP hybrid functional was used for obtaining radezolid spectra. Full identification was carried out by COSY, 1H 13C HSQC and 1H 13C HMBC experiments. The experimental NMR chemical shifts and spin-spin coupling constants were compared with theoretical calculations using the DFT method and B3LYP functional employing the 6-311++G(d,p) basis set and the solvent polarizable continuum model (PCM). The experimental ECD spectra of synthesized radezolid were compared with experimental spectra of the reference standard of radezolid. Theoretical calculations enabled us to conduct HOMO and LUMO analysis and molecular electrostatic potential maps were used to determine the active sites of microbiologically active form of radezolid enantiomer. The relationship between results of ab initio calculations and knowledge about chemical-biological properties of S-radezolid and other oxazolidinone derivatives are also discussed. Copyright © 2017 Elsevier B.V. All rights reserved.
Cechy publikacji
ORIGINAL_ARTICLE
Inne
System-identifier
826183
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