Synthesis of Selenium-Alkylated Selenocysteine Derivatives and Their Use in Native Chemical Ligation, Expressed Protein Ligation and the Synthesis of Dehydropeptides

Finally, an improved, scalable synthesis of Fmoc-phenylselenocysteine is reported. The amino acid was coupled to a model peptide on the solid phase. It was demonstrated that the selenide could be oxidatively eliminated to give a dehydropeptide while still bound to the solid resin. In addition, the peptide acted as a Michael acceptor for a thiol nucleophile. These solid phase reactions were monitored by magic angle spinning NMR spectroscopy.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Gieselman, Matthew Douglas

Contributors dc:contributor

• van der Donk, Wilfred A.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3101845

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84114