Synthesis of Delta(3)-Imidazolines as Latent Forms of Peptidyl Trifluoromethyl Ketones
Derstine, Christopher Wayne
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https://hdl.handle.net/2142/84363
Description
Title
Synthesis of Delta(3)-Imidazolines as Latent Forms of Peptidyl Trifluoromethyl Ketones
Author(s)
Derstine, Christopher Wayne
Issue Date
1997
Doctoral Committee Chair(s)
Katzenellenbogen, John 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, Pharmaceutical
Language
eng
Abstract
Many trifluoromethyl-substituted imidazolines were efficiently synthesized directly into larger peptides, by use of carbamate-protected amino acid fluorides as the initiator of the dipolar cycloaddition. The imidazolines then functioned as a protecting group for the trifluoromethyl ketones during typical peptide Fmoc deprotection and elongation reactions. In the final step, the imidazoline was hydrolyzed with dilute acid, which afforded the trifluoromethyl ketone in good yield. This process was carried out without the use of oxidants and was shown not to affect oxidizable species such as methionine.
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