Formation of 4,8-DiMeIQx from the model system fructose, alanine and creatinine. Comparison with the isomeric 5,8-DiMeIQx.
In a previous paper, the main mutagenic compound isolated from the model reaction system D-fructose, DL-alanine and creatinine was tentatively identified as 4,8-DiMeIQx. Its mutagenic activity and spectral characteristics have now been compared with those of the isomer 5,8-DiMeIQx. The comparison clearly demonstrates that the isolated compound was indeed 4,8-DiMeIQx. This finding is in agreement with the hypothesis that sugars, amino acids and creatinine present in meat may be the precursors of the mutagenic imidazoquinolin- and imidazoquinoxalin-2-amines (IQ compounds).
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Nyhammar
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Grivas
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Olsson
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Jägerstad
D000409:Alanine; D002851:Chromatography, High Pressure Liquid; D003404:Creatinine; D005632:Fructose; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D009153:Mutagens; D011810:Quinoxalines; D013329:Structure-Activity Relationship
D009153:Mutagens; D011810:Quinoxalines; C048764:3,5,8-trimethylimidazo(4,5-f)quinoxalin-2-amine; D005632:Fructose; D003404:Creatinine; D000409:Alanine; C045421:3,4,8-trimethylimidazo(4,5-f)quinoxalin-2-amine