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Peptide synthesis: evaluation of lipidic a-amino acids as drug and peptide delivery systems

Danton, Malcolm; (1996) Peptide synthesis: evaluation of lipidic a-amino acids as drug and peptide delivery systems. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

The α-amino acids with long alkyl side chains, the lipidic amino acids and their homo-oligomers, the lipidic peptides, represent a class of compounds which combine the structural properties of lipids with those of amino acids and peptides, such that they should possess a high degree of membrane-like character. One aim of this thesis was to evaluate the potential of lipidic α-amino acids and their peptides as drug and peptide delivery systems. It was envisaged that conjugation to selected compounds would result in increased lipophilic character for the latter, thereby assisting membrane penetration or translocation. Lipidic amino acids were synthesized and conjugated to baclofen, alanyl-glycine, lipid-core-peptide (LCP) system, luteinizing hormone-releasing hormone, and representative β-lactam antibiotics, by solution, and automated or manual solid phase methods, to give the lipidic conjugates of these compounds (baclofen was synthesized by the adaptation of a literature method). Biological evaluation of alanyl-glycine, LCP and β-lactam conjugates indicated that the lipidic moiety acted as a drug delivery system by penetrating membranes, to either anchor the active species to the membrane, or to translocate membranes. A further aim was to synthesize peptide fragments of the IgE receptor, as part of a long term project, in order to begin to understand the structure-function relationship. IgE receptor peptide fragments were synthesized for receptor topography studies, and for conformational studies.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Peptide synthesis: evaluation of lipidic a-amino acids as drug and peptide delivery systems
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Health and environmental sciences; A-amino; Acids; Amino; Delivery; Drug; Lipidic; Peptide
URI: https://discovery.ucl.ac.uk/id/eprint/10104925
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