Date of Award
Doctor of Philosophy
Peptide-alpha-phenylthioesters are particularly reactive starting materials for Native Chemical Ligation. Here we present a new photochemical method for the synThesis of peptide-alpha-phenylthioesters under neutral reaction conditions with various C-terminal amino acids. The peptides were synthesized by Fmoc strategy on Sieber amide resin with a photoreactive nitroindoline linker. After cleavage of the photoreactive and fully protected peptide from the beads with dilute trifluoroacetic acid an auxiliary nucleophile such as N-hydroxybenzotriazole or N-hydroxysuccinimide is used to photochemically generate the activated peptide ester in situ. Then thiophenol is introduced in the dark. This new method enabled us to synthesize peptide-alpha-phenylthioesters up to 21 amino acids long in good to high yields, and with low levels of epimerization at the C-terminal.
Received from ProQuest
Pardo, Andrew, "SynThesis Of Peptide-α-Phenylthioesters Using A Solid Support With A Photoreactive Nitroindoline Moiety" (2014). Open Access Theses & Dissertations. 1321.