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Description
Title: | I. Efforts Toward the Total Synthesis of (-)-Crambidine. II. Reactions of Azy(3-Me)-Containing Peptides With Thiols and Selenols |
Author(s): | Ide, Nathan D. |
Doctoral Committee Chair(s): | Gin, David Y. |
Department / Program: | Chemistry |
Discipline: | Chemistry |
Degree Granting Institution: | University of Illinois at Urbana-Champaign |
Degree: | Ph.D. |
Genre: | Dissertation |
Subject(s): | Chemistry, Organic |
Abstract: | An approach to (-)-crambidine, utilizing a key [4+2] annulation reaction between a thioimidate and an electron deficient vinyl carbodiimide, has been investigated. This approach has resulted in several advanced intermediates related to (-)-crambidine, but an efficient total synthesis of (-)-crambidine has not yet been completed. Additionally, an investigation into the base-promoted thiolysis and selenolysis of Azy(3-Me)-containing peptides has been performed. While thiols were found to have low reactivity with this class of electrophilic peptide residues, two S-linked glycopeptides were successfully synthesized. Benzeneselenol was found to be highly reactive with Azy(3-Me)-containing peptides, and a variety of synthetically useful selenopeptides have been generated. |
Issue Date: | 2006 |
Type: | Text |
Language: | English |
Description: | 340 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2006. |
URI: | http://hdl.handle.net/2142/84239 |
Other Identifier(s): | (MiAaPQ)AAI3242877 |
Date Available in IDEALS: | 2015-09-25 |
Date Deposited: | 2006 |
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