Formation of deaminated products in styrene oxide reactions with deoxycytidine.
The reaction of racemic styrene oxide with deoxycytidine under aqueous conditions was studied. The four principal products isolated were a pair of diastereomeric N(4)-(2-hydroxy-1-phenylethyl)deoxycytidines ( approximately 20% of the products) and a pair of diastereomeric 3-(2-hydroxy-2-phenylethyl)deoxyuridines ( approximately 80% of the products). Reactions with optically active styrene oxides allowed the configurations of the 3-(2-hydroxy-2-phenylethyl)deoxyuridines to be assigned, and these structures were confirmed by an independent synthesis from deoxyuridine. Also, it was possible to tentatively assign the configurations of the N(4)-(2-hydroxy-1-phenylethyl)deoxycytidines that had undergone some racemization during the reaction (the ratio of the retained to inverted configuration of the products was approximately 1:7).
Barlow
T
T
Chemistry of Carcinogenesis Laboratory, ABL-Basic Research Program, NCI-Frederick Cancer Research and Development Center, P.O. Box B, Frederick, Maryland 21702, USA.
Dipple
A
A
D000577:Amides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018736:DNA Adducts / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry*; D003857:Deoxyuridine / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D009153:Mutagens / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000577:Amides; D018736:DNA Adducts; D004852:Epoxy Compounds; D009153:Mutagens; D003841:Deoxycytidine; C013690:styrene oxide; D003857:Deoxyuridine