Abstract
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.
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