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Development of novel chiral stationary phases for use in chromatography
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Worsfold, Karen Elizabeth (1999) Development of novel chiral stationary phases for use in chromatography. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b1370642~S15
Abstract
The aim of this project was to prepare novel chiral stationary phases that could be investigated analytically by chromatography with a view to increasing to a preparative scale.
A summary of the different types of compounds used as chiral stationary phases as well as an introduction to chromatography as a method of separation is given, and a description of silica and PGC used as solid supports in chromatography. The suitability of PGC as a solid support is described, using a known stationary phase containing a phenyl carbamate derivative of cellulose.
The preparation of novel chiral stationary phases based on the polymerisation of chiral monomer units based on tartaric acid with diisocyanate linkers is described. Some of these compounds were tested using HPLC. However the reaction between monomer and diisocyanate linker resulted in a wide range of products such as macrocycles of different sizes which reduced the efficiency of the CSP.
The synthesis of a 1,4-functionalised sugar unit is described with a view to its polymerisation to form a saccharide polymer that could be used as a CSP.
The synthesis of novel macromolecules based on saccharide units linked with nonsaccharide linkers is described. The saccharide units used (glucose, cellobiose, maltose and maltotriose) were linked by a glycosidation reaction coupling the linker diol (1,4- trans-cyclohexanediol, 1,4-cis-2-butenediol and 1,4-butynediol) with the peracetylated sugar. Phenyl carbamate derivatives of these saccharide mimics were then prepared and tested for enantioselectivity by HPLC. Analysis by UV and CD spectroscopy was also carried out to investigate the secondary structures of these novel macromolecules.
An alternative method of loading the CSP onto the solid support was also investigated as well as atteq1pts at a larger scale separation.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Chirality., Stationary phase (Chromatography). | ||||
Official Date: | August 1999 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Clark, Andrew J. (Professor) | ||||
Sponsors: | Great Britain. Department of Trade and Industry ; Engineering and Physical Sciences Research Council ; Thermo Hypersil ; Tocris Cookson | ||||
Format of File: | |||||
Extent: | xvii, 257 pages : illustrations | ||||
Language: | eng | ||||
Date of first compliant deposit: | 1 April 2020 | ||||
Date of first compliant Open Access: | 1 April 2020 |
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