Date of Award

Summer 1966

Degree Type

Thesis - Restricted

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Vercellotti, John R.

Second Advisor

Hoffman, Norman

Third Advisor

Bournique, Raymond A.

Abstract

Glycoprotein and mucoprotein chemistry is and has been a subject of extensive interest and research. It is the purpose of this writing to describe the synthesis of a model compound, an 0-glycoside of an hydroxy amino acid, which as a postulate, forms a protein-to-carbohydrate linkage in glycoor mucoproteins. The 0-glycosides of suitably blocked 4-hydroxyproline and 2-amino-2-deoxy-D-glucopyranose (R-glucosamine) are one of a series of 0-glycosides of hydroxy-amino acids being synthesized and investigated by Dr. John R. Vercellotti of the department of chemistry of Marquette University. It is the premise of Dr. Vercellotti that an electron withdrawing group, such as the,2,4-dinitrophenyl group, linked to the amino function of the amino acid moiety in the Q-glycoside might simulate enzyme-substrate activity in the acid and base catalyzed hydrolysis of the 0-glycoside. It is hoped that the products of the hydrolysis of such suitably substituted and blocked 0-glycosides might provide basic information about the reactions of carbohydrates in i glycoproteins and their characterization.

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