Synthesis of Selenium-Alkylated Selenocysteine Derivatives and Their Use in Native Chemical Ligation, Expressed Protein Ligation and the Synthesis of Dehydropeptides
Gieselman, Matthew Douglas
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https://hdl.handle.net/2142/84114
Description
Title
Synthesis of Selenium-Alkylated Selenocysteine Derivatives and Their Use in Native Chemical Ligation, Expressed Protein Ligation and the Synthesis of Dehydropeptides
Author(s)
Gieselman, Matthew Douglas
Issue Date
2003
Doctoral Committee Chair(s)
van der Donk, Wilfred A.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
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.
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