title: Chiral recognition of N-phthaloyl, N-tetrachlorophthaloyl, and N-naphthaloyl α-amino acids and their esters on polysaccharide-derived chiral stationary phases.
abstract: Enantiomeric separations of N-phthaloyl (N-PHT), N-tetrachlorophthaloyl (N-TCPHT), and N-naphthaloyl (N-NPHT) α-amino acids and their esters were examined on several kinds of polysaccharide-derived chiral stationary phases (CSPs). Resolution capability of CSPs was greater Chiralcel OF than the others for N-PHT and N-NPHT α-amino acids and their esters. In N-TCPHT α-amino acids and their esters, good enantioselectivities showed Chiralcel OG for N-TCPHT α-amino acids, Chiralpak AD for N-TCPHT α-amino acid methyl esters, and Chiralcel OD for N-TCPHT α-amino acid ethyl esters, respectively. From the results of liquid chromatography and computational chemistry, it is concluded that l-form is preferred and more retained with electrostatic interaction in case of interaction between N-PHT α-amino acid derivatives and Chiralcel OF, N-TCPHT α-amino acid derivatives and Chiralcel OD, and N-NPHT α-amino acid derivatives and Chiracel OF. On the other hand, d-form is preferred and more retained with van der Waals interaction in case of interaction between N-TCPHT α-amino acid ester derivatives and Chiralcel OG and Chiralpak AD.
authors: Analytical Science, LG Chem. Research Park, LG Chem. Ltd., Yusong-Gu, Daejeon, South Korea. bhkime@gmail.com
authors: Byoung-Hyoun
authors: BH
authors: Kim
authors: Sang Uck
authors: SU
authors: Lee
authors: Dong Cheul
authors: DC
authors: Moon
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000302:isolation & purification*; D002853:Chromatography, Liquid / Q000379:methods*; D004952:Esters; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D011134:Polysaccharides