Investigations in the Praparation of Uronic Acid Sulphates

Abstract

Many naturally occurring carbohydrates contain sulphated uronic acid units, Very little is known about the structural properties of these sulphates uronic acid units. This work was concerned with the investigation of some methods of preparing the monosaccharide sulphates with a view to finding a method suitable for preparing model compounds. Sulphation reactions were carried out with D-glucuronic acid and D-galacturonic acid using three sulphating agents. Chlorosulphonic acid and pyridine sulphur trioxide complex gave some yield of uronic acid sulphate but no satisfactory method od purification was found. The unreacted starting material accompanied the sulphate at all Stages of work up. This effect may also have been complicated by hydrolysis of the uronic acid sulphate under the conditions used, Sulphuryl chloride did not appear to sulphate the uronic acids with the conditions used, except possibly, in very small amounts. Pectin and alginic acid when treated with sulphuryl chloride however did give a product with an appreciable sulphur and chlorine content and which probably contained a chloro- Sulphate of the polyuronic acid. A pure sample of D-mannuronic acid was prepared and the NMR spectra of D-glucuronic acid, D-galacturonic acid and D-matnorronic acid obtained. The following investigations were carried out at the University of Aston in Birmingham during the sessions 1964-1969. The author wishes to express his gratitude to Dr.A.Holt for his advice and encouragement during the supervision of this work. He also wishes to thank the University Authority and the staff of the Chemistry Department for the facilities provided and the ready acceptance of the inconvenience caused by part time research.