Use of topological descriptiors in chromatographic chiral separations

Abstract Studies of enantiomeric separations are reported, specifically the direct chromatographic separation of enantiomers using a chiral stationary phase by molecular topology. The results obtained show good correlation equations for the capacity factor, k ′, and the separation factor, α, for different set of compounds (hydantoins, aromatic α-amino acids and arylamides). Such equations may be useful for the selection of the optimum stationary and mobile phases for the separation of enantiomers. Futher, the correlation between topological descriptors and performance in chiral separations opens up a new approach to the design of chiral stationary phases.

[1]  J R Gillette,et al.  A comparison of the teratogenic activity of thalidomide in rabbits and rats. , 1968, The Journal of pharmacology and experimental therapeutics.

[2]  Jorge Gálvez,et al.  Charge Indexes. New Topological Descriptors , 1994, J. Chem. Inf. Comput. Sci..

[3]  J. Maguire Some structural requirements for resolution of hydantoin enantiomers with a beta-cyclodextrin liquid chromatography column. , 1987, Journal of chromatography.

[4]  Facundo Pérez-Giménez,et al.  Calculation of chromatographic parameters by molecular topology : sulphamides , 1994 .

[5]  G. M. A. Fos,et al.  Molecular topology and chromatographic retention parameters for benzodiazepines , 1992 .

[6]  H. Sobotka,et al.  OPTICALLY ACTIVE 5,5'-DISUBSTITUTED HYDANTOINS1 , 1932 .

[7]  L. Hall,et al.  Molecular connectivity in chemistry and drug research , 1976 .

[8]  D. Armstrong,et al.  Direct liquid chromatographic separation of racemates with an alpha-cyclodextrin bonded phase. , 1987, Analytical chemistry.

[9]  J. Maguire,et al.  Hypolipidemic activity of antiepileptic 5-phenylhydantoins in mice. , 1985, European journal of pharmacology.

[10]  L. Crane,et al.  Chromatographic chiral separations , 1988 .

[11]  T. Butler The metabolic conversion of 3-methyl-5-ethyl-5-phenyl hydantoin (mesantoin) and of 5-ethyl-5-phenyl hydantoin (nirvanol) to 5 - ethyl -5- (p-hydroxyphenyl) hydantoin. , 1956, The Journal of pharmacology and experimental therapeutics.

[12]  V. R. Meyer,et al.  New chiral, covalently bonded, π-donor stationary phases for high-performance liquid chromatography, based on derivatives of optically active 1-(α-naphthyl)ethylamine , 1986 .

[13]  L. Strekowski,,et al.  Amplification of bleomycin-mediated degradation of DNA by polyamines. , 1988, Anti-cancer drug design.

[14]  S. Unger Molecular Connectivity in Structure–activity Analysis , 1987 .