This thesis describes investigations towards the self-assembly of heterocyclic amino acids to form cyclopeptides, including the natural products dendroamide A and nostacyclamide. The Introduction highlights a variety of different natural products including the lissoclinum cyclopeptides and other oxazole and thiazole based natural products. The conformation of the lissoc1inum cyclopeptides and the affect different substituents have on their conformation is explored. The ability of a variety of natural products to chelate metal ions and the evidence for metal ion chelation within the lissoclinum cyclopeptides is also discussed. The Introduction is concluded with a statement of the aims and objectives of our research. The Results and Discussion section of the thesis details the development of a novel cyc1ooligomerisation reaction of heterocyclic amino acids. This cyc1ooligomerisation is applied to the self-assembly of thiazole and oxazole amino acids to form analogues of naturally occurring cyc1opeptides. The protocol is then extended to the self-assembly of the natural products dendroamide A and nostacyclamide. Additionally the ability of metal ions to act as templates and promote the formation of particular products is illustrated throughout these studies. Detailed discussions are also presented within this section into the methods for thiazole and oxazole formation. The third part of the thesis is the Experimental section containing full details of the preparative work completed and listing spectroscopic and analytical data on all new compounds synthesised during this study.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:342002 |
| Date | January 2001 |
| Creators | Bertram, Anna |
| Publisher | University of Nottingham |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://eprints.nottingham.ac.uk/13885/ |
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