Separation of fluorinated amino acids and oligopeptides from their non-fluorinated counterparts using high-performance liquid chromatography |
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Authors: | Nu Xiao |
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Affiliation: | a Department of Pharmaceutical Sciences, University of Maryland, Baltimore, MD 21201, United States b Fischell Department of Bioengineering, University of Maryland, College Park, MD 20742, United States |
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Abstract: | Chromatographic conditions for the separation of fluorinated amino acids and oligopeptides from their non-fluorinated counterparts were explored. The separation of six pairs of analytes, including both aromatic and aliphatic fluorocarbons, was investigated at various temperatures using both hydrocarbon and fluorocarbon columns and eluents. Our results show that when hydrocarbon eluents are used, fluorocarbon column provides better separation of fluorinated amino acids or oligopeptides from their non-fluorinated counterparts; when fluorocarbon eluents are used, hydrocarbon column provides better separation of fluorinated amino acids or oligopeptides from their non-fluorinated counterparts. These chromatographic behaviors reflect the fluorophilicity possessed by fluorinated amino acids and oligopeptides. |
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Keywords: | Cys, cysteine DCM, dichloromethane DIC, N,N&prime -diisopropylcarbodiimide DIPEA, N,N-diisopropylethylamine DMF, N,N-dimethylformamide EtOH, ethanol F%wt, fluorine weight percentage in an analyte or a solvent Fmoc, fluorenylmethoxycarbonyl HFIP, hexafluoroisopropanol HOBt, N-hydroxybenzotriazole HPLC, high-performance liquid chromatography ISP, isopropanol Lys, lysine MS, mass spectrometry MW, molecular weight Nle, norleucine NMR, nuclear magnetic resonance Nva, norvaline Phe, phenylalanine RPLC, reversed-phase liquid chromatography tBu, tert-butyl TFA, trifluoroacetic acid TFE, trifluoroethanol tfT, trifluorothreonine Thrallo, allo- smallcaps" >l-threonine tR, retention time Trp, tryptophan Trt, trityl Tyr, tyrosine δ, chemical shift ΔtR, retention time difference |
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