10.1016/S0040-4020(01)93166-7
The research investigates the synthesis and properties of N-nitroso derivatives of several amino acids. Sarcosine, azetidine-2-carboxylic acid, hydroxyproline, and pipecolic acid play crucial roles as the primary precursors for the synthesis of their respective N-nitroso derivatives. These derivatives are of significant interest due to their potential carcinogenic properties and their possible formation in the human stomach from dietary nitrites and amino acids. The study aims to understand the formation and characteristics of these nitrosamino acids, which could potentially be relevant to the occurrence of human cancer due to their possible formation in the mammalian stomach from dietary nitrites and amino acids. The researchers prepared these compounds and characterized them using various analytical techniques such as NMR spectroscopy, mass spectrometry, and UV absorption spectroscopy. They found that these compounds are colorless crystalline solids with high yields and are highly soluble in water and most organic solvents. The study also explored the conformational preferences of these compounds in the crystalline state and their behavior in different solvents. The findings suggest that these nitrosamino acids can decarboxylate in dilute alkali to form N-nitrosamines, which are known to be toxic and carcinogenic. The research concludes that the properties of these compounds could have significant implications for understanding the potential carcinogenic activity of nitrosamino acids formed in the human stomach.
