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Title: Synthesis and purification of peptides
Author: Irving, Stephen L.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1994
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Improved routes to tetrabenz[a,c,g,i]fluorene derivatives have been developed, allowing the synthesis of Nα-17-tetrabenzo[a,c,g,i]fluorenyl-methoxycarbonyl (tbfmoc) urethane derivatives of alanine, leucine, isoleucine, methionine and valine. The chloroformate and pentafluorophenyl carbonate of 17-tetrabenzo[a,c,g,]fluorenylmethanol have been prepared and used to introduce the base-labile Tbrmoc group onto the Nα-termini of resin-bound peptides. The high affinity of the Tbrmoc group for porous graphitised carbon (PGC) has been exploited for the purification of a range of synthetic peptides (23-85 residues). A comparison of various basic solvent systems used to elute the purified peptide from PGC is presented. The hydrophobicity of the Tbfmoc group has been used to simplify the purification of a ubiquitin analogue, UbY59F (76 residues), by the enhanced retention of the Tbfmoc peptide on RP-HPLC. A new synthesis of 2-hydroxydibenzocycloheptadien-5-one has been advised. This compound has been used to develop acid-labile linkers for the synthesis of peptide C-terminal alkyl amides and aza-glycine peptides, compatible with the Fmoc/tBu solid phase method. Alternative modes of attachment of the linker to polystyrene resin are compared for the synthesis of bombesin, a peptide amide.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available