Action of Hydroxylamine on Polysaccharides Oxidized with Periodic Acid

Abstract

BARRY¹ discovered that when a polysaccharide has been oxidized with periodic acid, the oxidation product on warming with phenylhydrazine yields glyoxalosazone. Thus, oxidized starch and cellulose are, theoretically at least, completely broken down into glyoxalosazone and erythrose phenylhydrazone, while 1,3 polysaccharides, such as laminarin, being attacked only at terminal units by periodic acid, have these oxidized terminal units completely removed by phenylhydrazine. It has now been found that a similar reaction takes place with hydroxylamine. Starch oxidized with periodic acid quickly dissolves in boiling water or absolute alcohol on addition of an alcoholic solution of hydroxylamine made by adding alcoholic potash to hydroxylamine hydrochloride until the solution is faintly alkaline. The solution becomes faintly acid as the starch dissolves and must be brought back to alkalinity by addition of more alcoholic potash. When the solution of the starch is complete, except for a small residue, the solvent is evaporated off, and ether will extract glyoxime from the residue after acidulation to set it free from its potassium compound.