Formation of Aromatic Compounds from Carbohydrates. VII. Reaction of D-Glucose and Glycine in Slightly Acidic, Aqueous Solution.

Abstract

The title reaction produced a humin-like precipitate. In the supernatant, D-fructose and compounds 1 - 27, comprising furans, pyrroles, pyridines, phenols, carboxylic acids and lactones were identified. 5-(Hydroxymethyl)pyrrole-2-carboxaldehyde (12), 2-formyl-5-methylpyrrole-1-acetic acid (14), 6-formyl-3,4-dihydro-3-oxopyrrolo[1,2-alpha]pyrazine-2(1H)aceticacid (16), 5-hydroxy-2-pyridyl methyl ketone (22) and 2-formyl-5-(5-formyl-2-furfuryloxymethyl)pyrrole-1-acetic acid (27) seem to be new compounds. 2-Methyl-3-pyridinol (17) and trans-5-(hydroxymethyl)-2-furanacrylic acid (25) have apparently not been identified previously as degradation products of carbohydrates. The formation of all 12 nitrogen compounds except 22 is rationalized by a reaction scheme, based on dehydration of the glucose, with or without Strecker degradation of the glycine.