The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures

The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures

When crystalline α-d-glucose prepared by crystallisation from cold concentrated acetic acid is dissolved in water its specific rotation is 113.4°, but slowly changes to 52.5°; β-d-glucose has an initial specific rotation of 17.5° which also changes to 52.5°. This phenomenon of mutarotation is shown...

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Main Author: Chapman, L. P. J.
Language:en
Published: University of Canterbury. Chemistry 2013
Online Access:http://hdl.handle.net/10092/8512
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spelling ndltd-canterbury.ac.nz-oai-ir.canterbury.ac.nz-10092-85122015-03-30T15:31:22ZThe catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixturesChapman, L. P. J.When crystalline α-d-glucose prepared by crystallisation from cold concentrated acetic acid is dissolved in water its specific rotation is 113.4°, but slowly changes to 52.5°; β-d-glucose has an initial specific rotation of 17.5° which also changes to 52.5°. This phenomenon of mutarotation is shown by a number of reducing sugars such as lactose and fructose. Lippmann and Simon first realised that a sugar having a cyclic (pyranose or furanose) structure should exist in two modifications differing in configuration about carbon atom one; Armstrong showed the structural relationship of α- and β-glucose to α- and β-methyl glucoside respectively; while Hudson and Lowry showed that mutarotation was due to the establishment of an equilibrium between the two forms in solution.University of Canterbury. Chemistry2013-10-28T20:06:35Z2013-10-28T20:06:35Z1946Electronic thesis or dissertationTexthttp://hdl.handle.net/10092/8512enNZCUCopyright L. P. J. Chapmanhttp://library.canterbury.ac.nz/thesis/etheses_copyright.shtml
collection NDLTD
language en
sources NDLTD
description When crystalline α-d-glucose prepared by crystallisation from cold concentrated acetic acid is dissolved in water its specific rotation is 113.4°, but slowly changes to 52.5°; β-d-glucose has an initial specific rotation of 17.5° which also changes to 52.5°. This phenomenon of mutarotation is shown by a number of reducing sugars such as lactose and fructose. Lippmann and Simon first realised that a sugar having a cyclic (pyranose or furanose) structure should exist in two modifications differing in configuration about carbon atom one; Armstrong showed the structural relationship of α- and β-glucose to α- and β-methyl glucoside respectively; while Hudson and Lowry showed that mutarotation was due to the establishment of an equilibrium between the two forms in solution.
author Chapman, L. P. J.
spellingShingle Chapman, L. P. J.
The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
author_facet Chapman, L. P. J.
author_sort Chapman, L. P. J.
title The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
title_short The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
title_full The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
title_fullStr The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
title_full_unstemmed The catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
title_sort catalytic effects of acetic acid-water mixtures on the mutarotation of α-d-glucose, and a comparison with the racemisation of 1-trans-αγ-dimethylglutaconic acid in acetic acid-water mixtures
publisher University of Canterbury. Chemistry
publishDate 2013
url http://hdl.handle.net/10092/8512
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