Document Type

Thesis

Date of Degree Completion

1967

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Chair

Robert D. Gaines

Second Committee Member

W. W. Newschwander

Third Committee Member

Wilber V. Johnson

Abstract

A series of phenyl-D-thioglucopyranosides were prepared and characterized in order to determine the absolute specificity of the .B-thioglucosidase and B-glucosidese enzyme systems toward the th1oglucosidic bond. The specificity of B-glucosidase of almond emulsin toward oxygen linkage seems to be absolute, since no hydrolysis was observed by this enzyme system toward the phenyl-D-thioglucopyranosides. The P-th1oglucosidase system was found to hydrolyze only two of the thioglucopyranosides. It was apparent that only where the electron-attracting substituents in the phenyl group were strong enough to greatly weaken the strength of the sulfur linkage, as in the case of the nitro group, would there be any hydrolysis. The lack of hydrolysis prevented application of the Hammett equation in testing the quantitative electronic effects of the substitutents on the rate of bond hydrolysis.

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Chemistry Commons

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