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dc.contributor.advisorKraatz, H-B.en_US
dc.creatorMilne, Mark Andrewen_US
dc.date.accessioned2009-03-13T16:01:41Zen_US
dc.date.accessioned2013-01-04T04:26:42Z
dc.date.available2010-04-14T08:00:00Zen_US
dc.date.available2013-01-04T04:26:42Z
dc.date.created2009en_US
dc.date.issued2009en_US
dc.date.submitted2009en_US
dc.identifier.urihttp://hdl.handle.net/10388/etd-03132009-160141en_US
dc.description.abstractIn 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 π-π interactions between intramolecular Dpp units as well as a number of CH-π 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 β-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 β-sheet like structures in solution.en_US
dc.language.isoen_USen_US
dc.subjectCyclicen_US
dc.subjectPeptidesen_US
dc.subjectFerroceneen_US
dc.titleSynthesis and Characterization of New Cyclic and Acylic Ferrocene Peptide Conjugatesen_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Saskatchewanen_US
thesis.degree.levelMastersen_US
thesis.degree.nameMaster of Science (M.Sc.)en_US
dc.type.materialtexten_US
dc.type.genreThesisen_US


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