Chemical synthesis of N-acetylgalactosamine-αI-phosphate 6-O-sulphate, N-acetylchondrosine sulphate and UDP-N-acetylgalactosamine6-O-sulphate

Abstract

The 6-O-sulphates of 2-acetamido-2-deoxy-α-D-galactose I-phosphate (N-acetylgalactosamine-αI-phoshate), $\text{O-(β-}\text{D}\text{-}\text{glucopyranosyluronic acid}\text{)-(}\text{I}\text{→3)-2-}\text{acetamido}\text{-2-}\text{deoxy}\text{-}\text{D}\text{-}\text{galactase}$ (N-acetylchondrosine) and UDP-2-acetamido-2-deoxy-α-D-galactose (UDP-N-acetylgalactosamine) were synthesized using triethylamine-N-sulphonic acid as sulphating agent. The products of the reaction were purified by fractionation on ECTEOLA-cellulose and converted to the barium salts by passage through the barium form of a cation-exchange resin. Evidence for the homogeneity of the sulphates was provided by chemical analysis, paper chromatography, electrophoresis, colorimetric assay and infrared spectra. Proof for the position of the sulphate group on the primary hydroxyl of the N-acetylhexosamines was provided by periodate consumption studies and the detection of glycolaldehyde sulphate as an end product of periodate oxidation.