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.

Date of Award	1972
Original language	English
Awarding Institution	Aston University