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A new class of phosphate-esterified alpha-hydroxyalkyl-alkyl-nitrosamines is described. Here we report the synthesis of these compounds. The mechanism of their formation from the corresponding alpha-acetoxy compounds, and starting from alpha-hydroperoxy compounds is studied by monitoring the reactions in the u.v.-spectrophotometer, by reaction with alkaline phosphatase and by determination of aldehydes generated during degradation of the N-nitrosoacetylesters. Their stability in aqueous solution and their phosphatase-induced degradation was determined. It was found that alpha-phosphate-nitrosamines are more stable in aqueous solution than the alpha-acetates or the parent alpha-hydroxy compounds. Therefore their role as intermediates in nitrosamine metabolism is discussed.
N Frank, and
M Wiessler
November 1963,
Arzneimittel-Forschung,
N Frank, and
M Wiessler
February 2000,
Bioorganic & medicinal chemistry,
N Frank, and
M Wiessler
January 1984,
IARC scientific publications,
N Frank, and
M Wiessler
February 1982,
Ecotoxicology and environmental safety,
N Frank, and
M Wiessler
January 1976,
Annales de la nutrition et de l'alimentation,
N Frank, and
M Wiessler
March 1975,
Toxicology and applied pharmacology,
N Frank, and
M Wiessler
January 1977,
Voprosy onkologii,
N Frank, and
M Wiessler
September 1996,
European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP),
