Direct enantiomeric resolution of cyclic alcohol derivatives of polycyclic aromatic hydrocarbons by chiral stationary phase high-performance liquid chromatography.
The enantiomers of some cyclic alcohol derivatives of phenanthrene, benz[a]anthracene, benzo[a]pyrene, cholanthrene, and 3-methylcholanthrene were resolved by high-performance liquid chromatography using a commercially available preparative column packed with an (R)-N-(3,5-dinitrobenzoyl)phenylglycine ionically bonded to gamma-aminopropylsilanized silica. Resolution of enantiomers was confirmed by ultraviolet-visible absorption, mass and circular dichroism spectral analyses. This method has been applied to the determination of optical purity of 1-hydroxycholanthrene and 1-hydroxy-3-methylcholanthrene formed in the metabolism of cholanthrene and 3-methylcholanthrene, respectively, by rat liver microsomes.
D000818:Animals; D001551:Benz(a)Anthracenes / Q000032:analysis; D001564:Benzo(a)pyrene; D001580:Benzopyrenes / Q000032:analysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D008748:Methylcholanthrene / Q000031:analogs & derivatives / Q000032:analysis / Q000378:metabolism; D009153:Mutagens; D010616:Phenanthrenes / Q000032:analysis; D011083:Polycyclic Compounds / Q000032:analysis*; D051381:Rats; D013237:Stereoisomerism
D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D009153:Mutagens; D010616:Phenanthrenes; D011083:Polycyclic Compounds; D001564:Benzo(a)pyrene; C031181:phenanthrene; D008748:Methylcholanthrene; C037411:benz(j)aceanthrylene; C030935:benz(a)anthracene