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

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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.

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