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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 |
Doctoral Committee Chair(s): | van der Donk, Wilfred A. |
Department / Program: | Chemistry |
Discipline: | Chemistry |
Degree Granting Institution: | University of Illinois at Urbana-Champaign |
Degree: | Ph.D. |
Genre: | Dissertation |
Subject(s): | Chemistry, Organic |
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. |
Issue Date: | 2003 |
Type: | Text |
Language: | English |
Description: | 134 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003. |
URI: | http://hdl.handle.net/2142/84114 |
Other Identifier(s): | (MiAaPQ)AAI3101845 |
Date Available in IDEALS: | 2015-09-25 |
Date Deposited: | 2003 |
This item appears in the following Collection(s)
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Dissertations and Theses - Chemistry
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Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois