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Date of Award
Master of Science (M.S.)
O. Bertrand Ramsey
First Committee Member
W. Hugh Wadman
Second Committee Member
Emerson G. Cobb
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.
Pizanis, Michael James. (1963). Hydrolysis of alpha-D-glucosamine-l-phosphate. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/382