Hydrolysis of alpha-D-glucosamine-l-phosphate
type: CreativeWork
description: 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: 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.
author: Pizanis, Michael James
keywords: Phosphates, Glucosides, Hydrolysis, Amines, Chemistry, Physical Sciences and Mathematics
license: http://rightsstatements.org/vocab/NKC/1.0/
date published: 1963-01-01T08:00:00Z
date modified: 2026-07-24T05:36:21Z
provider: University of the Pacific
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: University of the Pacific