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