Synthesis of peptide-alpha-phenylthioesters using a solid support with a photoreactive nitroindoline moiety | Posted on:2015-10-22 | Degree:Ph.D | Type:Thesis | University:The University of Texas at El Paso | Candidate:Pardo, Andrew | Full Text:PDF | GTID:2474390020450932 | Subject:Chemistry | Abstract/Summary: | | 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. | Keywords/Search Tags: | Peptide-alpha-phenylthioesters, Photoreactive | | Related items |
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