Investigation on enantiomeric separations of fluorenylmethoxycarbonyl amino acids and peptides by high-performance liquid chromatography using native cyclodextrins as chiral stationary phases.
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-beta-alanyl-Cl. All derivatives were chromatographed on native beta- and gamma-cyclodextrin columns using acetonitrile as the main mobile phase component. The results indicated that glycyl and beta-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 type of chiral stationary phase employed exhibited significant impacts on chiral resolutions. It is also found that the number and position of glycyl moieties affect the retentions and enantioselectivities of FMOC derivatized glycyl containing peptides.
Tang
Y
Y
Department of Chemistry, University of Missouri Rolla 65401, USA.
Zukowski
J
J
Armstrong
D W
DW
D000409:Alanine / Q000737:chemistry; D000596:Amino Acids / Q000032:analysis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D009842:Oligopeptides / Q000032:analysis; D013237:Stereoisomerism
D000596:Amino Acids; D003505:Cyclodextrins; D005449:Fluorenes; D007202:Indicators and Reagents; D009842:Oligopeptides; C054007:1-(9-fluorenyl)methyl chloroformate; D000409:Alanine; D005998:Glycine; D000432:Methanol