A Chemical Procedure for Determination of the C¹⁴-Distribution in Labeled Glucose

A procedure based on the work of Jackson and Hudson was developed for the degradation of methyl-α-D-glucopyranoside formed from 2 millimoles of glucose. Oxidation of the glucoside with periodic acid gave C-3 as formic acid and a dialdehyde which was converted to the strontium salt of D′-methoxy-D-hydroxymethyl diglycolic acid. The purified salt was hydrolyzed to glyoxylic and glyceric acids. The glyoxylic acid was isolated as the 2,4-dinitrophenylhydrazone (C-1 + C-2); this was decarboxylated by heat to give carbon dioxide from C-2. The glyceric acid was oxidized by periodate to give C-4 as carbon dioxide, C-5 as formic acid, and C-6 as formaldehyde. This degradation permitted the determination of C 14 in each position of the glucose molecule, the activity in C-1 being determined by difference. The method was applied to glucose-1-C 14 and a sample of glucose labeled in all positions with satisfactory results.