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Chemical Compound Review:

AC1L3GNK (1-nitroso-2-piperidyl) ethanoate

Synonyms: AR-1C4920, AC1Q6R9N, alpha-Acetoxynpip, alpha-Acetoxy-N-nitrosopiperidine, (1-nitrosopiperidin-2-yl) acetate, ...

Wang, M. et al., Young-Sciame, R. et al.

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High impact information on alpha-Acetoxy-N-nitrosopiperidine

The goal of this study was to compare the reactions of alpha-acetoxy-N-nitrosopyrrolidine (alpha-acetoxyNPYR) and alpha-acetoxy-N-nitrosopiperidine (alpha-acetoxyNPIP) with deoxyguanosine (dG). alpha-AcetoxyNPYR and alpha-acetoxyNPIP are stable precursors to the alpha-hydroxynitrosamines which are formed metabolically from NPYR and NPIP [1].
Reaction of alpha-acetoxyNPIP with DNA followed by enzyme hydrolysis and HPLC analysis resulted in the positive identification of two diastereomers of N2-(3,4,5,6-tetrahydro-2H-pyran-2-yl)deoxyguanosine (THP-dG) by comparison of their retention times and UV spectra to those of standards [2].
We studied the reactions with DNA of alpha-acetoxy-N-nitrosopyrrolidine (alpha-acetoxyNPYR) and alpha-acetoxy-N-nitrosopiperidine (alpha-acetoxyNPIP) in order to obtain more information on adduct formation by metabolic activation via alpha-hydroxylation of two cyclic nitrosamines, N-nitrosopyrrolidine (NPYR) and N-nitrosopiperidine (NPIP) [2].

Biological context of alpha-Acetoxy-N-nitrosopiperidine

Neutral thermal hydrolysis of DNA that had been reacted with alpha-acetoxyNPIP produced 2-hydroxy-3,4,5,6-tetrahydro-2H-pyran (THP-OH) [2].

References

Reactions of alpha-acetoxy-N-nitrosopyrrolidine and alpha-acetoxy-N-nitrosopiperidine with deoxyguanosine: formation of N2-tetrahydrofuranyl and N2-tetrahydropyranyl adducts. Young-Sciame, R., Wang, M., Chung, F.L., Hecht, S.S. Chem. Res. Toxicol. (1995) [Pubmed]
Formation of N2-tetrahydrofuranyl and N2-tetrahydropyranyl adducts in the reactions of alpha-acetoxy-N-nitrosopyrrolidine and alpha-acetoxy-N-nitrosopiperidine with DNA. Wang, M., Young-Sciame, R., Chung, F.L., Hecht, S.S. Chem. Res. Toxicol. (1995) [Pubmed]

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