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Separation of fluorinated amino acids and oligopeptides from their non-fluorinated counterparts using high-performance liquid chromatography
Authors:Nu Xiao
Institution: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
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.
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  l-threonine" target="_blank">allo-l-threonine  tR  retention time  Trp  tryptophan  Trt  trityl  Tyr  tyrosine  δ  chemical shift  ΔtR  retention time difference
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