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Tytuł pozycji:

Silver (I)-dimercaptotriazine functionalized silica: A highly selective liquid chromatography stationary phase targeting unsaturated molecules.

Tytuł :
Silver (I)-dimercaptotriazine functionalized silica: A highly selective liquid chromatography stationary phase targeting unsaturated molecules.
Autorzy :
Liao S; Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Dillon JT; Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Huang C; Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Santos E; Department of Earth, Environmental and Planetary Sciences, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Huang Y; Department of Earth, Environmental and Planetary Sciences, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA. Electronic address: .
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Źródło :
Journal of chromatography. A [J Chromatogr A] 2021 May 24; Vol. 1645, pp. 462122. Date of Electronic Publication: 2021 Mar 30.
Typ publikacji :
Journal Article
Język :
English
Imprint Name(s) :
Original Publication: Amsterdam ; New York : Elsevier, 1993-
MeSH Terms :
Chromatography, Liquid/*methods
Silver Compounds/*chemistry
Sulfhydryl Compounds/*chemistry
Triazines/*chemistry
Fatty Acids, Unsaturated/analysis ; Fatty Acids, Unsaturated/isolation & purification ; Fatty Acids, Unsaturated/metabolism ; Silver Compounds/metabolism ; Sulfhydryl Compounds/metabolism ; Triazines/metabolism
Contributed Indexing :
Keywords: Lipid analysis; Silver ion chromatography; Silver(I)-dimercaptotriazine; Silver-thiolate chromatography; Van't Hoff plots
Substance Nomenclature :
0 (Fatty Acids, Unsaturated)
0 (Silver Compounds)
0 (Sulfhydryl Compounds)
0 (Triazines)
Entry Date(s) :
Date Created: 20210414 Date Completed: 20210507 Latest Revision: 20210507
Update Code :
20210508
DOI :
10.1016/j.chroma.2021.462122
PMID :
33853010
Czasopismo naukowe
Silver(I)-mercaptopropyl (Ag-MP) functionalized silica gel has demonstrated its effectiveness in separating various unsaturated organic compounds including unsaturated fatty acid ethyl esters (FAEEs), triglycerols (TAGs) and long-chain alkyl ketones (alkenones). While Ag-MP stationary phase displays many advantages over the conventional silver ion-impregnated silica gel (e.g., stability, high recovery, etc.), potential drawbacks of Ag-MP include relatively low retentions for unsaturated molecules, which could limit chromatographic resolutions under certain circumstances. In this study, we evaluate a new silver-thiolate stationary phase: silver(I)-dimercaptotriazine (Ag-DMT) functionalized silica gel targeting the separation of unsaturated compounds. We show Ag-DMT affords substantially higher retention factors, peak resolutions and capacities for TAGs and FAEEs than Ag-MP does. Ag-DMT also yields higher purity eicosapentaenoic acid (EPA) from fish oil FAEE mixtures than Ag-MP. In addition, Ag-DMT resolves double bond positional and cis/trans-isomers of C 18:1 fatty acid methyl esters (FAMEs) as well as unsaturated methyl/ethyl alkenones with different number of double bonds. Based on van't Hoff plots, enthalpy changes during the adsorption of unsaturated FAEEs onto Ag-DMT are ~2 times higher than those on Ag-MP. Such difference may be attributed to the stronger electron-withdrawing effect of the thiol group on DMT, which results in more positively charged silver ions hence greater interactions with unsaturated molecules. The stronger interaction between double bonds and Ag-DMT is further corroborated by density-functional theory (DFT) calculations. Ag-DMT shows its high stability for repeated uses in the separation of TAGs over 319 runs, with peak resolutions decreasing by < 3%. Collectively, our data demonstrate the exceptionally high efficiency of Ag-DMT column for separating unsaturated molecules.
(Copyright © 2021. Published by Elsevier B.V.)

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