Chemical characteristics of N-aminated nucleic acid bases. Nitrosation of aromatic N-amino group and accompanying reductive deamination.
Primary NH2 group attached to the pyridine-type or pyrrole-type nitrogen underwent sequential nitrosation and reductive deamination by the treatment with NaNO2-AcOH. Secondary NHR group attached to the pyridine-type nitrogen underwent also the reductive deamination. In contrast, secondary NHR group attached to the pyrrole-type nitrogen gave the corresponding N-nitroso derivative under the same conditions. Mechanism of the reductive deamination is discussed.
Hasebe
K
K
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Kohda
K
K
D000588:Amines / Q000737:chemistry*; D003641:Deamination; D015538:Nitrosation; D009696:Nucleic Acids / Q000737:chemistry*; D010084:Oxidation-Reduction
D000588:Amines; D009696:Nucleic Acids