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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


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