Prebiotic synthesis of imidazole-4-acetaldehyde and histidine.
The prebiotic synthesis of imidazole-4-acetaldehyde and imidazole-4-glycol from erythrose and formamidine has been demonstrated as well as the prebiotic synthesis of imidazole-4-ethanol and imidazole-4-glycol from erythrose, formaldehyde and ammonia. The products were identified by TLC, HPLC, and LC-MS by comparison with authentic samples. The maximum yields of imidazole-4-acetaldehyde, imidazole-4-ethanol, and imidazole-4-glycol obtained in these reactions are 1.6, 5.4, 6.8% respectively, based on the erythrose. Imidazole-4-acetaldehyde would have been converted to histidine on the primitive earth by a Strecker synthesis, and several prebiotic reactions would convert imidazole-4-glycol and imidazole-4-ethanol to imidazole-4-acetaldehyde.
D000447:Aldehydes; D000641:Ammonia; D002851:Chromatography, High Pressure Liquid; D005557:Formaldehyde; D006639:Histidine; D007093:Imidazoles; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D013780:Tetroses
D000447:Aldehydes; D007093:Imidazoles; D007202:Indicators and Reagents; D013780:Tetroses; D005557:Formaldehyde; D006639:Histidine; C053546:1H-imidazole-4-acetaldehyde; D000641:Ammonia