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Investigation of Hydrolytic Deamination of 1-(-Hydroxy-1-Phenylethyl)Adenosine

  1. Author:
    Barlow, T.
    Ding, J. M.
    Vouros, P.
    Dipple, A.

  2. Author Address

    Barlow T NCI FREDERICK CANC RES & DEV CTR ABL BASIC RES PROGRAM CHEM CARCINOGENESIS LAB POB B FREDERICK, MD 21702 USA NORTHEASTERN UNIV BARNETT INST DEPT CHEM BOSTON, MA 02115 USA
    1. Year: 1997
  2. Journal: Chemical Research in Toxicology
    1. 10
    2. 11
    3. Pages: 1247-1249
  4. Type of Article: Article
  1. Abstract:

    The ring nitrogen of adenosine reacts at both the alpha-(benzylic) and beta-carbons of styrene oxide to form 1-substituted products. The 1-(2-hydroxy-1-phenylethyl)adenosines formed by oxirane ring opening at the alpha-position are prone to an unusually facile hydrolytic deamination. By conducting hydrolysis reactions in [O-18]water and analyzing the reaction products by electrospray mass spectrometry, we find that deamination occurs by direct attack of water at the beta-position of the adenine ring system with displacement of the exocyclic amino group. [References: 16]

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