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.
","abstract_html":"<p>Some information on the hydrolysis mechanism of phosphate esters was obtained by studying the kinetics of ∝-D-Glucosamine-1-phosphate.</p><p>∝-D-Glucosamine-1-phosphate was synthesized, an experimental pH-rate profile for the hydrolysis of this phosphate was determined at 100 C.</p><p>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.</p><p>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.</p>","abstract_has_math":false,"creators":["Pizanis, Michael James"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["O. Bertrand Ramsey"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1963,"date_issued":"1963-01-01T08:00:00Z","date_published":"1963-01-01T08:00:00Z","updated_at":"2026-07-24T05:36:21Z","subjects":["Phosphates","Glucosides","Hydrolysis","Amines","Chemistry","Physical Sciences and Mathematics"],"languages":[],"rights":[],"rights_urls":["http://rightsstatements.org/vocab/NKC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://scholarlycommons.pacific.edu/uop_etds/382","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["O. Bertrand Ramsey"]},{"key":"dc:creator","label":"Author","values":["Pizanis, Michael James"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2018-06-29T08:41:53Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Phosphates","Glucosides","Hydrolysis","Amines","Chemistry","Physical Sciences and Mathematics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["http://rightsstatements.org/vocab/NKC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarlycommons.pacific.edu/uop_etds/382"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:source","label":"Dc Source","values":["52"]},{"key":"dc:title","label":"Title","values":["Hydrolysis of alpha-D-glucosamine-l-phosphate"]}]}],"canonical_facts":{"dc:contributor":["O. Bertrand Ramsey"],"dc:creator":["Pizanis, Michael James"],"dc:date.available":["2018-06-29T08:41:53Z"],"dc:description.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.
"],"dc:identifier":["https://scholarlycommons.pacific.edu/uop_etds/382"],"dc:rights":["http://rightsstatements.org/vocab/NKC/1.0/"],"dc:source":["52"],"dc:subject":["Phosphates","Glucosides","Hydrolysis","Amines","Chemistry","Physical Sciences and Mathematics"],"dc:title":["Hydrolysis of alpha-D-glucosamine-l-phosphate"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T05:36:21Z"}