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Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase
Thesis (MSc (Chemistry and Polymer Science))--University of Stellenbosch, 2007.
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| Format: | Thesis |
| Language: | English |
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Stellenbosch : University of Stellenbosch
2007
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| _version_ | 1867614117557174272 |
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| access_status_str | Open Access |
| author | De Villiers, Jandre |
| author2 | Strauss, Erick |
| author_browse | De Villiers, Jandre Strauss, Erick |
| author_facet | Strauss, Erick De Villiers, Jandre |
| author_sort | De Villiers, Jandre |
| collection | Thesis |
| dc_rights_str_mv | University of Stellenbosch |
| description | Thesis (MSc (Chemistry and Polymer Science))--University of Stellenbosch, 2007. |
| format | Thesis |
| id | oai:scholar.sun.ac.za:10019.1/3096 |
| institution | Stellenbosch University (South Africa) |
| language | English |
| last_indexed | 2026-06-10T12:46:56.603Z |
| license_str | Other — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from SUNScholar — Stellenbosch University Repository |
| publishDate | 2007 |
| publishDateRange | 2007 |
| publishDateSort | 2007 |
| publisher | Stellenbosch : University of Stellenbosch |
| publisherStr | Stellenbosch : University of Stellenbosch |
| record_format | dspace |
| source_str | SUNScholar — Stellenbosch University Repository |
| spelling | oai:scholar.sun.ac.za:10019.1/3096 Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase De Villiers, Jandre Strauss, Erick Jardine, Anwar University of Stellenbosch. Faculty of Science. Dept. of Chemistry and Polymer Science. Dissertations -- Chemistry Theses -- Chemistry Ornithine -- Synthesis Ornithine decarboxylase Fluorination Thesis (MSc (Chemistry and Polymer Science))--University of Stellenbosch, 2007. Human African Trypanosomiasis (HAT) is a disease that threatens more then 60 million men, woman and children in Africa. It is known that the inhibition of the enzyme, ornithine decarboxylase (ODC) leads to cell arrest and subsequent death of Trypanosoma brucei, the parasite that causes the disease. The fluorinated ornithine analogue, DFMO (difluoromethylornithine or eflornithine) is a known inhibitor of ODC. Although various syntheses for DFMO exist they have some practical drawbacks which prevent the cost effective production of this compound as a drug for HAT treatment. This work focuses on the synthetic preparation of the fluorinated ornithine analogue DFMO as well as the fluorinated ornithine analogues 2-MFMO, 3-fluoro-ornithine and 3,3-difluoro-ornithine. Our chosen synthetic methodology focused on the introduction of the fluorine functionality using a simpler, safer and more convenient method than current direct fluorination techniques, or those that rely on the use of CFCs. Instead we decided to develop and optimise a fluorodehydroxylation method based on the transformation of hydroxylated ornithine analogues. The fluorodehydroxylation method substitutes a hydroxyl group to the corresponding fluorine and can also be used to transform an aldehyde or ketone to the corresponding difluoro group. Application of this fluorination method requires the synthesis of appropriate ... 2007-11-27T13:46:40Z 2010-06-01T09:06:11Z 2007-11-27T13:46:40Z 2010-06-01T09:06:11Z 2007-03 Thesis http://hdl.handle.net/10019.1/3096 en University of Stellenbosch 745465 bytes application/pdf application/pdf Stellenbosch : University of Stellenbosch |
| spellingShingle | Dissertations -- Chemistry Theses -- Chemistry Ornithine -- Synthesis Ornithine decarboxylase Fluorination De Villiers, Jandre Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title | Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title_full | Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title_fullStr | Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title_full_unstemmed | Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title_short | Attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| title_sort | attempted routes towards the synthesis of fluorinated analogues of ornithine as potential inhibitors of ornithine decarboxylase |
| topic | Dissertations -- Chemistry Theses -- Chemistry Ornithine -- Synthesis Ornithine decarboxylase Fluorination |
| url | http://hdl.handle.net/10019.1/3096 |
| work_keys_str_mv | AT devilliersjandre attemptedroutestowardsthesynthesisoffluorinatedanaloguesofornithineaspotentialinhibitorsofornithinedecarboxylase |