ICCAS OpenIR
Phosphonic drugs: Experimental and theoretical spectroscopic studies of fosfomycin
Chruszcz-Lipska, Katarzyna1; Zborowski, Krzysztof K.1; Podstawka-Proniewicz, Edyta1; Liu, Shaoxuan2; Xu, Yizhuang2; Proniewicz, Leonard M.1,3
2011-02-14
Source PublicationJOURNAL OF MOLECULAR STRUCTURE
ISSN0022-2860
Volume986Issue:1-3Pages:49-56
AbstractpH and time-dependant changes of fosfomycin molecular structure in an aqueous solution are studied by Raman. NMR, and generalized 2D correlation spectroscopies. Interpretation of the experimental spectra is based on the assumption of formation of different species running on applied physicochemical conditions. Geometries of all possible structures were entirely optimized with the 6-311++G(2df,p) basis set at the B3LYP theoretical level using procedures implemented in the Gaussian '03 set of programs. Harmonic frequency calculations verified the nature of the studied structures and allowed to simulate obtained Raman spectra. The theoretical NMR shielding was calculated using the GIAO method at the same computational level. In addition, in some cases PCM model was used to monitor the influence of water molecules on the NMR spectra. It is shown that in the pH range of 1-2 of fosfomycin aqueous solution oxirane ring is open sequent to nucleophilic attack and forms 1,2-dihydroxyphosphonic acid with small content of its monodeprotonated species. On the other hand, in pH 7 and higher it appears either as 1,2-epoxypropylphosphonic or 1,2-dihydroxyphosphonic dianion depending upon whether hydrolysis took place or not. It is also discussed that Raman marker bands originating from the individual species of fosfomycin can be used to detect and/or to monitor this antibiotic in an aqueous medium (for example urine samples). Hence, depending upon the structure found in urine one can tell about metabolic processes of this antibiotic in the body. (C) 2010 Elsevier B.V. All rights reserved.
KeywordFosfomycin Raman Spectroscopy Nmr Spectroscopy Generalized 2d Correlation Analysis Theoretical Calculations
DOI10.1016/j.molstruc.2010.11.033
Indexed BySCI
Language英语
WOS IDWOS:000287075100007
PublisherELSEVIER SCIENCE BV
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/72242
Collection中国科学院化学研究所
Corresponding AuthorProniewicz, Leonard M.
Affiliation1.Jagiellonian Univ, Fac Chem, PL-30060 Krakow, Poland
2.Peking Univ, Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
3.State Higher Vocat Sch, PL-33100 Tarnow, Poland
Recommended Citation
GB/T 7714
Chruszcz-Lipska, Katarzyna,Zborowski, Krzysztof K.,Podstawka-Proniewicz, Edyta,et al. Phosphonic drugs: Experimental and theoretical spectroscopic studies of fosfomycin[J]. JOURNAL OF MOLECULAR STRUCTURE,2011,986(1-3):49-56.
APA Chruszcz-Lipska, Katarzyna,Zborowski, Krzysztof K.,Podstawka-Proniewicz, Edyta,Liu, Shaoxuan,Xu, Yizhuang,&Proniewicz, Leonard M..(2011).Phosphonic drugs: Experimental and theoretical spectroscopic studies of fosfomycin.JOURNAL OF MOLECULAR STRUCTURE,986(1-3),49-56.
MLA Chruszcz-Lipska, Katarzyna,et al."Phosphonic drugs: Experimental and theoretical spectroscopic studies of fosfomycin".JOURNAL OF MOLECULAR STRUCTURE 986.1-3(2011):49-56.
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