Michael Heidelberger as a Carbohydrate Chemist

The deoxyaldaric acids corresponding in structure to the 3-deoxy-2-C-(hydroxymethyl)aldonic (isosaccharinic) acids have been identified as products of treatment of various carbohydrates with alkali and oxygen-alkali. The structures of the acids were determined from the mass spectra of their Me₃Si derivatives on the basis of previously known, specific fragmentation reactions. The g.l.c.-m.s. technique was used, and g.l.c. retention data are given. The identified species are 2-deoxy-3-C-(hydroxymethyl)tetraric, 3-deoxy-2-C-hydroxymethyl-erythro-pentaric, 3-deoxy-2-C-hydroxymethyl-threo-pentaric, 2-methyltartronic, 2-(2-hydroxyethyl)tartronic, and 2-(2,3-dihydroxypropyl)tartronic acids. Their formation from 4-O-substituted uronic and ulosonic acids is briefly discussed.