Optical resolution of enantiomeric amino acid derivatives on a naphthylethylurea multiple-bonded chiral stationary phase prepared via an activated carbamate intermediate.
A new chiral stationary phase (CSP) was developed for the direct optical resolution of enantiomeric amino acid derivatives. The CSP was readily prepared by a three-step reaction carried out in a pre-packed aminopropylsilyl silica gel column. In the first step, a solution of disuccinimido carbonate (DSC) was delivered through the pre-packed column to give a succinimido carbamyl aminopropylsilyl-bonded, activated-carbamate type silica gel (ACsil) column. Through the column was then delivered a solution of pentaethylenehexamine to afford a polyamine-bonded column. Finally, a solution of optically active succinimido (S)- or (R)-naphthylethyl carbamate was delivered through the polyamine column, to give a naphthylethylurea multiple-bonded CSP. p-Bromophenylcarbamyl derivatives of enantiomeric protein amino acids were resolved on these CSPs by elution with an aqueous mobile phase. Simultaneous analysis of these amino acid enantiomers by means of gradient elution was also accomplished.
Iwaki
K
K
Laboratory of Analytical Chemistry, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
Yoshida
S
S
Nimura
N
N
Kinoshita
T
T
Takeda
K
K
Ogura
H
H
D000596:Amino Acids / Q000032:analysis*; D002219:Carbamates / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009281:Naphthalenes; D013237:Stereoisomerism; D014508:Urea
D000596:Amino Acids; D002219:Carbamates; D007202:Indicators and Reagents; D009281:Naphthalenes; D014508:Urea