In this thesis a series of diphenol phenanthroline (Dpp) peptide conjugates were synthesized and then coupled to ferrocene to give the corresponding organometallic conjugates. The first step of the synthesis was achieved by esterification of peptides with the phenol group of the Dpp. The next step was the removal of the protecting Boc group and the addition of ferrocene acid chloride at high dilutions to give the desired macrocycles of the type Dpp-(peptide)2 Fc. (peptide = Leu-Leu (3), Leu-Leu-Leu (5) ). However, the syntheses proceeded in low yields where only small quantities of the desired products were obtained. A suitable crystal of compound 3 was grown from CHCl3 which shows a number of intra and intermolecular hydrogen bonding interactions between peptides strands.In addition, the system [Dpp-Fc]2 (1) was syntheised by refluxing Dpp and Fc[COCl]2 in dichloromethane. A suitable crystal was grown which has ð-ð interactions between intramolecular Dpp units as well as a number of CH-ð interactions which determine the crystal packing. The electrochemical experiments on compound 1 show a cathodic shift upon addition of Zn2+ to a solution of 1. This observation is believed to occur because of a conformational change in 1. The last area of synthesis that was done was the attempt at â-sheet formation using Fc as a scaffold to align peptide strands. Two systems were studied in this thesis [Fc(n-AA-OMe)(1-AA)]2-1,4butyl diamine. (AA =Ala (8), Gly (9)). Both were studied by 1H NMR to evaluate the presence of hydrogen bonding interactions. The results indicate the presence of intramolecular H-bonding, which is believed to form â-sheet like structures in solution.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:SSU.etd-03132009-160141 |
| Date | 14 April 2009 |
| Creators | Milne, Mark Andrew |
| Contributors | Kraatz, H-B. |
| Publisher | University of Saskatchewan |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | http://library.usask.ca/theses/available/etd-03132009-160141/ |
| Rights | unrestricted, I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to University of Saskatchewan or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report. |
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