Activator Free C-to-N Solid Phase Peptide Synthesis

2023 Undergraduate Research Symposium

Liz Ballmann (chemistry) and Lawernce Mendoza

Faculty mentor: Jennifer Stockdill

Abstract

Peptides have been gaining traction as lead drug targets due to their ability to disrupt protein-protein interactions and contain fewer off-target effects. Methodologies to synthesize peptides have been well-established since the development of Merrifield's Solid-Phase Peptide Synthesis (SPPS). As the demand to access therapeutic peptides have increased over the years, greener methods of assembling peptides have not caught up to alleviate the consumption of excess reagent required in SPPS.

Novel approaches for assembling peptides utilizing minimal amounts of reagents are needed in the peptide field without sacrificing overall product yield and purity. N-Acyl Ureas (NAU) have been shown to be easily displaced by exogenous nucleophiles and are less prone to epimerization than current methodologies in the literature. Herein, we developed an approach harnessing the reactivity NAUs to diversify the assembly of peptides in an economical fashion.

Poster

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Liz Ballmann: Activator Free C-to-N Solid Phase Peptide Synthesis

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