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    Novel Organophosphorus Oligomers. Synthesis and conformation of ¿-hydroxy phenylphosphinates.

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    Publication date
    2013-12-05
    Author
    Royappa, Martin
    Supervisor
    Afarinkia, Kamyar
    Keyword
    Organophosphorus oligomers
    Synthesis
    ¿-hydroxy phenylphosphinates
    Rights
    Creative Commons License
    The University of Bradford theses are licenced under a Creative Commons Licence.
    Institution
    University of Bradford
    Department
    Institute of Cancer Therapeutics
    Awarded
    2010
    
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    Abstract
    Chapter one reviews the recent progress in the synthesis of phosphonopeptides, pseudopeptides containing a phosphinic, phosphonic or phosphonamide linkage in place of an amide (peptide) linkage. It describes some of the general methods for the synthesis of these pseudopeptides; for example through couplings to the nitrogen of an ¿-aminophosphonic acid, or Michael addition to acrylates, as well as other methods, the scope for which are not as wide yet. It also provides a summary of the reported biological activities of this class of pseudopeptides. Chapter two contains the results and discussion for a novel method for the synthesis of ¿-hydroxy phenylphosphinate oligomers as well as hybrid oligomers containing ¿-hydroxy phenylphosphinic acid and ¿-amino carboxylic acids. In particular, synthesis of a series of dimeric ¿-hydroxy phenylphosphinates are reported. The analysis of these dimers by a combination of NMR spectroscopy, X-ray crystallography and computational methods shows intramolecular hydrogen bonding in these molecules depends on the relative configuration of the carbon and phosphorus atoms. However, although the development of the synthetic methods was successful, the separation and isolation of the diastereomers was not always possible, which hindered a more comprehensive analysis of folding patterns in these molecules. Chapter three contains the experimental procedures, preparation and spectroscopic characterisation of all the chemical compounds. Crystal data and details of crystal structures are in the Appendix.
    URI
    http://hdl.handle.net/10454/5748
    Type
    Thesis
    Qualification name
    PhD
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    Theses

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