N-nitroso-hydroxyalkyl-alkylamine phosphate esters--a new class of N-nitroso compounds.
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.
D000469:Alkaline Phosphatase / Q000378:metabolism; D002021:Buffers; D002273:Carcinogens; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D009602:Nitrosamines / Q000138:chemical synthesis*; D010755:Organophosphates / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D010710:Phosphates; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet
D002021:Buffers; D002273:Carcinogens; D009602:Nitrosamines; D010755:Organophosphates; D009943:Organophosphorus Compounds; D010710:Phosphates; D012996:Solutions; D000469:Alkaline Phosphatase