Resolution of epoxide enantiomers of polycyclic aromatic hydrocarbons by chiral stationary-phase high-performance liquid chromatography.
Enantiomers of nine K-region and one non-K-region epoxides of polycyclic aromatic hydrocarbons have been resolved by high-performance liquid chromatography with chiral stationary phases either ionically or covalently bonded to gamma-aminopropylsilanized silica. Resolution of enantiomers was confirmed by ultraviolet-visible absorption, circular dichroism, and mass spectral analyses. This method has been applied to the determination of optical purity and absolute configuration of the K-region epoxides formed in the metabolism of 1-methylbenz[a]anthracene, 7-methylbenz[a]anthracene, and 12-methylbenz[a]anthracene by rat liver microsomes.
D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002942:Circular Dichroism; D004852:Epoxy Compounds / Q000302:isolation & purification* / Q000378:metabolism; D004988:Ethers, Cyclic / Q000302:isolation & purification*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D011083:Polycyclic Compounds / Q000302:isolation & purification* / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D011083:Polycyclic Compounds