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 ...
| Identifer | oai:union.ndltd.org:netd.ac.za/oai:union.ndltd.org:sun/oai:scholar.sun.ac.za:10019.1/3096 |
| Date | 03 1900 |
| Creators | De Villiers, Jandre |
| Contributors | Strauss, Erick, Jardine, Anwar, University of Stellenbosch. Faculty of Science. Dept. of Chemistry and Polymer Science. |
| Publisher | Stellenbosch : University of Stellenbosch |
| Source Sets | South African National ETD Portal |
| Language | English |
| Detected Language | English |
| Type | Thesis |
| Format | 745465 bytes, application/pdf |
| Rights | University of Stellenbosch |
Page generated in 0.0025 seconds