title: Comparison of the isolation of adducts of 2'-deoxycytidine and 2'-deoxyguanosine with phenylglycidyl ether by high-performance liquid chromatography on a reversed-phase column and a polystyrene-divinylbenzene column.
abstract: 2'-Deoxycitidine (dCyd) and 2'-deoxyguanosine (dGuo) were subjected to reaction with phenylglycidyl ether (PGE) in methanol in order to study the formation of the corresponding 2'-deoxynucleoside adducts. Separation methods were developed on analytical and semi-preparative scales using high-performance liquid chromatography with photodiode-array detection on a reversed-phase column and on a polystyrene-divinylbenzene column. The use of the latter column was prompted by decomposition of the preparatively isolated dGuo-PGE adducts on the reversed-phase column. The use of a polystyrene-divinylbenzene column solved this problem and also revealed the presence of one more peak in both the dCyd- and dGuo-PGE reaction mixtures. The adducts of dCyd and dGuo were isolated on preparative reversed-phase and polystyrene-divinylbenzene columns and characterized by UV, fast atom bombardment mass and 360 MHz 1H NMR spectrometry. The adducts of dCyd were the diastereomers of N-3-(2-hydroxy-3-phenoxypropyl)-2'-deoxycytidine and N4-(2-hydroxy-3-phenoxypropyl)-2'-deoxycytidine whereas those of dGuo were the two diastereomers of N-7-(2-hydroxy-3-phenoxypropyl)-2'-deoxyguanosine and a third peak which appeared to be mainly N2-(2-hydroxy-3-phenoxypropyl)-2'-deoxyguanosine.
authors.affiliation: College of Pharmacy, University of Ghent, Belgium.
authors.forename: E
authors.initials: E
authors.lastname: van den Eeckhout
authors.forename: J
authors.initials: J
authors.lastname: Coene
authors.forename: J
authors.initials: J
authors.lastname: Claereboudt
authors.forename: F
authors.initials: F
authors.lastname: Borremans
authors.forename: M
authors.initials: M
authors.lastname: Claeys
authors.forename: E
authors.initials: E
authors.lastname: Esmans
authors.forename: J E
authors.initials: JE
authors.lastname: Sinsheimer
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification*; D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000737:chemistry / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D010647:Phenyl Ethers; D003841:Deoxycytidine; C016050:phenylglycidyl ether; D003849:Deoxyguanosine