Preparation of Dehydropeptides and Their Application in the Convergent Synthesis of Peptide Conjugates

Beyond its utility in the preparation of lantibiotics, this method is also well suited for the preparation of peptide conjugates. The functionalities encountered in natural amino acids include nucleophilic, acidic, and basic groups, but no electrophilic moieties. Thus, introduction of an electrophilic group into peptides will provide a handle for the chemoselective incorporation of nucleophiles. Based on this analysis, a convergent route involving site-specific modification of the unprotected dehydropeptide (the electrophilic handle) by Michael additions of suitable nucleophiles was developed. The C-terminal sequence of N-Ras, a number of other lipid peptides and S-linked glycopeptides were prepared through the Michael addition of corresponding thiolates to dehydropeptides. Furthermore, the preparation of dehydropeptides and the Michael addition were also illustrated to be compatible with solid phase.

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

• Zhu, Yantao

Contributors dc:contributor

• van der Donk, Wilfred A.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3102013

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84123