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The synthesis of fluorinated carbohydrates and fluorinated cyclohexanols

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
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

Identifiers

Local EPrints ID: 366976
URI: http://eprints.soton.ac.uk/id/eprint/366976
PURE UUID: 1571167e-17e5-42ab-b658-ece61f9cc223
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 22 Oct 2014 10:36
Last modified: 06 Jun 2018 12:52

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Contributors

Author: Lewis Mtashobya
Thesis advisor: Bruno Linclau ORCID iD

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