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Title: A linker approach to heterocyclic amino acids
Author: Crumpling, Lisa Jane
ISNI:       0000 0001 3399 3000
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 2005
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Polypeptide Nucleic Acids, PNAs, are analogues of DNA and have the potential to bind to DNA by base-pairing and hence act as therapeutic agents. Amino acids carrying heterocycles in their side-chains are valid targets as natural products and as components of these potential therapeutic agents (PNAs) for use in living organisms. The aim of this investigation was to synthesise a range of heterocyclic amino acids, that could be used in the formation of PNAs. The proteinogenic amino acids, serine and cysteine and the unnatural amino acids, homocysteine, 2,3-diaminopropionic acid and 2,4-diaminobutyric acid, have been used in the formation of said heterocyclic amino acids via a C-X bond (where X=C, S, O or N) in a linker chain. It was decided to approach the synthesis of heterocyclic amino acids by way of a linker approach, joining the ready-formed heterocycle with an amino acid. Once the amino acids had been suitably protected several different methods were attempted in order to form heterocyclic amino acids. To form a carbon-carbon (X=C) bond in the linker chain, radical and organocuprate conjugate addition reactions and hydroboration and metathesis coupling were attempted. The formation of a linker containing a carbon-heteroatom bond (X=S, O or N) was investigated using a substitution approach.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available