Isotopically-enriched carbohydrates: The preparation of [2H]-enriched aldoses by catalytic hydrogenolysis of cyanohydrins with 2H2

Abstract

A procedure is described for the preparation of aldoses and aldose phosphates enriched with 2H by hydrogenolysis of aldononitriles and aldononitrile phosphates over palladium using 2H2. Aldoses, aldose phosphates, and derivatives prepared with 13C and (or) 2H enrichment and characterized by 1H and 13C nmr were: DL-[1-14C, 2H]glyceraldehyde, D-[1-13C, 2H]erythrose, D-[1-13C, 2H]threose, D-[2-13C, 2H]ribose, D-[2-13C, 2H]arabinose, methyl α-D-[2-13C, 2H]ribofuranoside, methyl β-D-[2-13C, 2H]ribofuranoside, DL-[3-2H]erythrose, DL-[3-2H]threose, DL-[1-13C, 2H]glyceraldehyde 3-phosphate, and D-[1-13C, 2H]ribose 5-phosphate. 13C isotope shifts, 1H and 13C chemical shifts, and homo- and heteronuclear coupling constants are reported.