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Title: The design of a new heterocyclic coupling agent for peptide synthesis
Author: Davison, Amanda
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1993
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The subject matter of this thesis is concerned with investigations on the synthesis of N-hydroxytriazoles and their potential use as auxiliary nucleophiles in peptide synthesis. Synthetic routes to four N-hydroxytriazoles; 1-hydroxy-5-methyl-4-phenyl-1 H-1,2,3-triazole, 1-hydroxy-4-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole, ethyl 1-hydroxy-5-methyl-1H-1,2,3-triazole-4-carboxylate, ethyl 1-hydroxy-1H-1,2,3-triazole-4-carboxylate and two N-hydroxyimidazoles; 2,5-dimethyl-1-hydroxy-4-phenyl-1H-imidazole and 1-hydroxy-2-methyl-4-phenyl-1H-imidazole were developed. 2,5-Dimethyl-4-phenyl-1H-imidazole was tested as a potential mediator in peptide synthesis by the attempted synthesis of the simple test peptide LeuIIePheAlaGly but was found to be unsuitable in this respect. Therefore investigations were concentrated on the N-hydroxytriazoles. The N-hydroxytriazoles were generally more soluble in solvents compatible with the peptide synthesiser (eg. DMF and DMF:dioxane) than the N-hydroxyimidazoles. All of the N-hydroxytriazoles synthesised were tested for use as potential auxiliary nucleophiles in the synthesis of LeuIIePheAlaGly and were found to be capable of mediating peptide bond formation as successfully as HOBt. Ethyl 1-hydroxy-5-methyl-1H-1,2,3-triazole-4-carboxylate and ethyl 1-hydroxy-1H-1,2,3-triazole-4-carboxylate were also evaluated as coupling agents for the amino acid sequences found in peptides such as Substance P, luteinizing hormone releasing hormone (LHRH) and nerve growth factor (NGF) 100-114.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available