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Formation of deaminated products in styrene oxide reactions with deoxycytidine

  1. Author:
    Barlow, T.
    Dipple, A.

  2. Author Address

    Barlow T MRC, Mol Biol Lab Hills Rd Cambridge CB2 2QH England NCI, Frederick Canc Res & Dev Ctr, ABL Basic Res Program, Chem Carcinogenesis Lab Frederick, MD 21702 USA
    1. Year: 1999
  2. Journal: Chemical Research in Toxicology
    1. 12
    2. 10
    3. Pages: 883-886
  4. Type of Article: Article
  1. Abstract:

    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 (similar to 20% of the products) and a pair of diastereomeric 3-(2-hydroxy-2-phenylethyl)deoxyuridines (similar to 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 similar to 1:7). [References: 26]

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