• 약학회지
• /
• 제33권2호
• /
• pp.129-139
• /
• 1989

New diamide chiral stationary phases of four systematically substituted optically active N-(N-benzoyl-L-amino acid)-anilide synthesized from L-valine, L-leucine, L-isoleucine, and L-phenylalanine were described. The behaviors of these diamides as optically active stationary phases for the separation of N-trifluoroacetyl-D,L-amino acids were examined with respect to separation factors(${\alpha}$) and thermodynamic properties of interaction. The separation of twelve N-trifluoroacetyl-D,L-amino acid isopropyl esters were improved by the order of N-(N-benzoyl-L-leucyl)-anilide>N-(N-benzoyl-L-isoleucyl)-anilide>N-(N-benzoyl-L-valyl)-anilide>N-(N-benzoyl-L-phenylalanyl)-anilide. Eight amino acid derivatives with non-polar R-group and threonine, serine, aspartic acid, and glutamic acid enantiomers were separated on N-(N-benzoyl-L-leucyl)-anilide as chiral stationary phase with good separation factor between 1.07-1.25. The separation factors decreased with respect to increasing column temperature. Possible working temperature of diamide phase was between $130-190^{\circ}C$ for N-(N-benzoyl-L-phenylalanyl)-anilide and $130-180^{\circ}C$ for other three diamide phases. The differential Gibb's free energy (${\Delta}{\Delta}G$) of enantiomers was in the range of -100--180 cal/mol for ten amino acids and -40--60 cal/mol for alanine and aspartic acid.

• 약학회지
• /
• 제29권6호
• /
• pp.375-379
• /
• 1985

The gas chromatographic behavior of optically active N-(N-benzoyl-L-valyl)-anilide used as stationary phase is described. N-(N-benzoyl-L-valyl)-anilide has been synthesized with good yield under mild condition via Schotten-Bauman process and coated on the Chromosorb W AW (80-100mesh) for the purpose of enantiomer separation. The behavior of this compound as optically active stationary phase for the separation of the enantiomers of N-TFA-D, L-amino acid isopropyl esters has been examined with respect to the correlation between the separation factors and column temperatures. All amino acid enantiomers examined were eluted within one hour and the elution pattern showed retention times increasing in the order of alanine, valine, leucine, threonine, proline and methionine.

• Archives of Pharmacal Research
• /
• 제12권1호
• /
• pp.58-61
• /
• 1989

Studies of selectivity of hydrogen bond formation in chiral solute-solvent systems have been performed by $^1H\;and\;^{13}C$ nuclear magnetic resonance techniques. These data are correlated with the results of gas chromatographic investigations of the same systems. Interactions between the optically active solvent(N-(N-benzoyl-L-amino acid)-anilide) and optically active solute (N-trifluoroacetyl -L-alanyl isopropyl ester) were examined. NMR evidence indicated that hydrogen bonding interaction occurred between two N-H portion and on peptidyl carbonyl portion in stationary phase and solute molecule on three points. The association constants of solvent-solute interaction were calculated and the structure of the diastereomeric association complex between N-(N-benzoyl-L-valyl)-anilide and N-TFA-L-alanyl isopropyl ester was proposed.