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Hydrolysis of alpha-D-glucosamine-l-phosphate

Author

Michael James Pizanis, University of the Pacific

Date of Award

1963

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Chemistry

First Advisor

O. Bertrand Ramsey

First Committee Member

W. Hugh Wadman

Second Committee Member

Emerson G. Cobb

Abstract

Some information on the hydrolysis mechanism of phosphate esters was obtained by studying the kinetics of ∝-D-Glucosamine-1-phosphate.

∝-D-Glucosamine-1-phosphate was synthesized, an experimental pH-rate profile for the hydrolysis of this phosphate was determined at 100 C.

It was proposed that Species I (see page 7) had P-O cleavage with intramolecular proton transfer to ester oxygen. Species II is believed to have the same mechanism of hydrolysis as monoanion of methyl phosphate and monoanion of ∝-D-Glucosamine-1-phosphate. This study indicates that Species III s reactive, while the dianion of methyl phosphate and the dianion of ∝-D-Glucosamine-1-phosphate are inactive. The increased reactivity of Species III may be accounted for by the ability for proton transfer to ester oxygen.

This investigator concluded that the amino group of ∝-D-Glucosamine-1-phosphate has an appreciable effect on the ease of P-O and C-O cleavage and the position of rate maximum.

Pages

52

Recommended Citation

Pizanis, Michael James. (1963). Hydrolysis of alpha-D-glucosamine-l-phosphate. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/382