The reaction of 3-0-substituted sugars with aqueous ammonia. 4-(Imidazol-4-yl)butane-1,2,3-triol and its mass spectrum

Abstract

3-Deoxy-D-glucosone, 3-0-methyl-D-glucose, and turanose react with aqueous ammonia to form L-erythro-4-(imidazol-4-yl)butane-1,2,3-triol as the major basic product. A mechanism is proposed for the formation of this imidazole from hexose disaccharides, and its mass spectrum is discussed.