Chemistry of Non-Enzymic Browning. VIII. The Hydrolytic reactions of Aldose Bisulphite addition compounds

Abstract

A study has been made of the hydrolytic reactions of aldose bisulphite addition compounds (Ingles 1959a, 19596). Addition compounds which had a hydroxyl group at C₁ were stable in 10 per cent, acetic acid but decomposed in water and sodium hydroxide forming the a-form of the parent D-aldose. Compounds in which the hydroxyl at C₁ was replaced by an amine group were unstable in water, 10 per cent. acetic acid, and sodium hydroxide. In the last solvent breakdown to the α-form of the D-glycosylamine was observed. Decomposition in sodium hydroxide appears to occur with inversion of configuration at C₁. The configurations at C₁ of the bisulphite addition compounds have been listed.