Chemical synthesis of N-acetylhexosamine 6-sulfates

The 6-sulfates of N-acetylglucosamine and N-acetylgalactosamine were synthesized using triethylamine-N-sulfonic acids as the sulfating agent. The products of the reaction were purified by fractionation on an anion-exchange column, desalted by means of an ion-retardation resin and converted to the barium salts by passage through the barium form of a cation-exchange resin. Evidence for the homogeneity of the 6-sulfates was provided by chemical analysis, paper chromatography. electrophoresis, colorimetric assay and infrared spectra. Proof for the position of the sulfate group on the primary hydroxyl of the N-acetylhexosamines was provided by periodate consumption studies, the detection of glycolaldehyde sulfate as an end product of periodate oxidation and comparison with a sample of N-acetylglucosamine 6-sulfate synthesized by an unambiguous route. The latter product was prepared via the 6-trityl intermediate as described in the text.