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Title: Industrial, chemical and biological aspects of phosphorus-containing heterocycles
Author: Snip, Erwin
Awarding Body: University of Leicester
Current Institution: University of Leicester
Date of Award: 1999
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This thesis presents three different topics in phosphorus-containing heterocycles. The first topic is about novel phosphorus-containing flame-retardants to be used in poly-urethane foams. The background and importance of flame-retardants is discussed as well as the synthesis and testing data of compounds that were expected to have good flame-retardant properties. More importantly, these compounds represent a class of flame-retardants that can be chemically incorporated into the polymer, which will overcome current negative aspects such as leaching and fogging. The test results show that the tested compounds perform about as well as commercially available materials and that there are indications that they are chemically incorporated into the polymer. The second topic is about the cytotoxic effects of aziridines. The phosphate moiety of a DNA-chain can act as a nucleophile that ring-opens an aziridine. This reaction results in the formation of a phosphate triester with a potential nucleophile, namely an amino group, in a beta-position. These two factors make the hydrolysis of the DNA chain at this particular point much more likely. A model study was designed to investigate the likelihood of DNA-chain cleavage by aziridines as these form an important class of anti-tumour agents. From this model study it can be concluded that the cytotoxic effects of aziridines have to be contributed to alkylation of other nucleophilic sites at DNA than to strand cleavage preceded by alkylation of the phosphate backbone. The last topic covers a stereochemical investigation of the metal catalysed hydrolysis of a cyclic nucleotide. It presents the first stereochemical assignment of the metal catalysed hydrolysis of a phosphate ester. In line with most enzyme catalysed hydrolyses of phosphate esters the reaction investigated here was assigned to go with inversion of configuration.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available