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Towards synthetic peptide ligation.

Morris, T.W.; (2008) Towards synthetic peptide ligation. Doctoral thesis , University of London. Green open access

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Abstract

Presented is a novel protocol for the ligation of protected peptide segments that relies on a selective ruthenium-catalyzed cross metathesis reaction. Amino acid A-termini were acryloylated using acryloyl chloride and triethylamine and C-termini were coupled to homoallylamine using standard coupling conditions. The conditions used in both reactions are suited to use on protected peptides. Model studies were performed on a range of single protected amino acids. This demonstrated the applicability of the technique. The synthetic ligation between a protected dipeptide bearing a C-terminal homoallyl amide and a protected 7V-acryloyl tripeptide was achieved. Application to the total chemical synthesis of modified Crambin was then investigated. A site was chosen for ligation and syntheses of the appropriate peptide segments were attempted using solid phases peptide synthesis techniques and an Fmoc protection approach.

Type: Thesis (Doctoral)
Title: Towards synthetic peptide ligation.
Identifier: PQ ETD:591824
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1444518
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