Two alternative compounds have been prepared and studied, as alternatives to the benzyl amine in the preparation of hemoglobin bis-tetramers. The reactivity of these compounds towards the activated ester groups on trimesoyl tris(3,5-dibromosalicylate), and 3,5-dibromosalicylate benzyl ester has been studied, as well as their functionality in a range of acidic solutions. Initial rate kinetics was used to determine rate constants for hydrazinolysis, and hydrolysis of the two esters. The objective was to find a suitable functional group that would be less basic than the benzyl amine yet still exhibit good nucleophilicity in the preparation of hemoglobin bis-tetramers. Hydrolysis being the main side reaction limiting the yield, could be slowed down in an acidic solution, but the nucleophile used could not be protonated in the process. It has been found that the benzyl hydrazine was the most effective and able to react with cross-linked hemoglobin to give the most product.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/30178 |
| Date | 01 December 2011 |
| Creators | Bator, Daniel |
| Contributors | Kluger, Ronald |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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