Physical Sciences and Mathematics Commons^™

Investigation On Enantiomeric Separations Of Fluorenylmethoxycarbonyl Amino Acids And Peptides By High-Performance Liquid Chromatography Using Native Cyclodextrins As Chiral Stationary Phases, Y. Tang, J. Zukowski, Daniel W. Armstrong

Chemistry Faculty Research & Creative Works

A systematic study was carried out to investigate enantiomeric separations of fluorenylmethoxycarbonyl (FMOC) amino acids and their peptides. Twenty amino acids were derivatized by 9-fluorenylmethyl chloroformate (FMOC-Cl) and its analogues, FMOC-glycyl-Cl and FMOC-β-alanyl-Cl. All derivatives were chromatographed on native β- and γ-cyclodextrin columns using acetonitrile as the main mobile phase component. The results indicated that glycyl and β-alanyl groups between FMOC and amino acid moieties enhanced chiral selectivities of amino acid derivatives. The addition of modifiers, triethylamine, acetic acid and methanol, into the mobile phase caused alterations in retention, enantiorecognition and elution order. The structures of amino acids and the …