CARBON-13-ENRICHED CARBOHYDRATES - PREPARATION OF ERYTHROSE, THREOSE, GLYCERALDEHYDE, AND GLYCOLALDEHYDE WITH C-13-ENRICHMENT IN VARIOUS CARBON-ATOMS

Two-, three-, and four-carbon aldononitriles were prepared, and catalytically reduced with palladium-barium sulfate (5%) to the coresponding aldoses in high yields at pH 1.7 ± 0.1 and atmospheric pressure. Carbon-13-enriched glycolaldehyde, glyceraldehyde, erythrose, and threose were prepared with enrichment in various carbon atoms, permitting unequivocal assignment of chemical shifts for all carbons and determination of the proportions of cyclic hemiacetals and linear gem-diol forms in solution. Carbon-carbon and carbon-hydrogen coupling-constants for the furanose ring and linear hydrates of these short-chain aldoses are reported and discussed. © 1979.