Synthesis of Delta(3)-Imidazolines as Latent Forms of Peptidyl Trifluoromethyl Ketones

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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Derstine, Christopher Wayne

Contributors dc:contributor

• Katzenellenbogen, John A.

• Chemistry, Pharmaceutical

Language dc:language

eng

Identifier

(MiAaPQ)AAI9737088

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84363