A mutagenic metabolite synthesized by Salmonella typhimurium grown in the presence of azide is azidoalanine.
A mutagenic azide metabolite was purified from the medium in which Salmonella typhimurium cells were grown in the presence of azide. This metabolite was identified to be azidoalanine based on infrared and mass spectroscopy and elemental analysis. This compound appeared to be identical to the mutagenic compound synthesized in vitro from azide and O-acetylserine by partially purified O-acetylserine sulfhydrylase. The metabolite (azidoalanine) mutagenic efficiency and spectrum in S. typhimurium was similar to that of inorganic azide. The compounds 2-azidoethylamine, 2-bromoethylamine, 3-bromopropionic acid and N-(azidomethyl) phthalimide were also mutagenic with a similar spectrum to azide and azidoalanine, but with lower efficiency. The compounds 3-azidopropylamine, 4-azidobutylamine, 3-chloroalanine and ethylamine were only weakly or nonmutagenic. Numerous other chloro, bromo and azido phthalimide derivatives tested were nonmutagenic. It is suggested that the lack of azide mutagenicity (and perhaps carcinogenicity) in mammalian cells may be due to their inability to convert azide to azidoalanine.
D000409:Alanine / Q000031:analogs & derivatives* / Q000032:analysis / Q000096:biosynthesis* / Q000494:pharmacology; D001386:Azides / Q000032:analysis / Q000096:biosynthesis* / Q000378:metabolism* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D003470:Culture Media / Q000378:metabolism; D013058:Mass Spectrometry; D009152:Mutagenicity Tests; D009153:Mutagens / Q000032:analysis / Q000378:metabolism* / Q000494:pharmacology; D012486:Salmonella typhimurium / Q000187:drug effects / Q000378:metabolism*; D013055:Spectrophotometry, Infrared
D001386:Azides; D003470:Culture Media; D009153:Mutagens; C039309:azidoalanine; D000409:Alanine