The synthesis of fluorinated carbohydrates and fluorinated
cyclohexanols
The synthesis of fluorinated carbohydrates and fluorinated
cyclohexanols
Carbohydrates are central to many fundamental processes. However, their interactions to proteins are characterized by low binding affinity. An attractive strategy to improve this affinity is polyfluorination of carbohydrates. This thesis describes the synthesis and extensive NMR characterisation of monoand difluorinated 2,3-dideoxysugars in which a sugar (CHOH)(CHOH) section was replaced with the more hydrophobic CH2CHF, CH2CF2 and CHFCHF groups. An important consequence of sugar fluorination is that the hydrogen bond properties of the adjacent alcohol group(s) are modified. Part of this thesis describes the synthesis of a number of fluorinated cyclohexanol and benzyl alcohol derivatives as probes to investigate the influence of fluorination on the alcohol hydrogen bond donating capacity.
Mtashobya, Lewis
7e000614-c31f-43fb-96da-75bf6cf2076d
April 2014
Mtashobya, Lewis
7e000614-c31f-43fb-96da-75bf6cf2076d
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Mtashobya, Lewis
(2014)
The synthesis of fluorinated carbohydrates and fluorinated
cyclohexanols.
University of Southampton, Chemistry, Doctoral Thesis, 182pp.
Record type:
Thesis
(Doctoral)
Abstract
Carbohydrates are central to many fundamental processes. However, their interactions to proteins are characterized by low binding affinity. An attractive strategy to improve this affinity is polyfluorination of carbohydrates. This thesis describes the synthesis and extensive NMR characterisation of monoand difluorinated 2,3-dideoxysugars in which a sugar (CHOH)(CHOH) section was replaced with the more hydrophobic CH2CHF, CH2CF2 and CHFCHF groups. An important consequence of sugar fluorination is that the hydrogen bond properties of the adjacent alcohol group(s) are modified. Part of this thesis describes the synthesis of a number of fluorinated cyclohexanol and benzyl alcohol derivatives as probes to investigate the influence of fluorination on the alcohol hydrogen bond donating capacity.
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Published date: April 2014
Organisations:
University of Southampton, Chemistry
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Local EPrints ID: 366976
URI: http://eprints.soton.ac.uk/id/eprint/366976
PURE UUID: 1571167e-17e5-42ab-b658-ece61f9cc223
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Date deposited: 22 Oct 2014 10:36
Last modified: 15 Mar 2024 05:02
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Author:
Lewis Mtashobya
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