Synthesis of Peptoids with Varying Alkyl Side Chains and Urea Functional Groups

Abstract

Peptoids are N-substituted glycines that act as biomimetic analogs to peptides. Peptoids, like peptides, demonstrate significant changes in conformation based on the substituents attached to them. Whether a peptoid backbone has a cis or trans conformation is a significant factor in how they take shape as larger molecules. This aspect of conformation in peptoids is especially significant as an area of study as it can affect the compound’s ability to self-aggregate and form nanomaterials, including helices, turns, and nanosheets. Given the importance of cis and trans conformations, this was a strong focus of the NMR analysis done as part of this research. Urea is a small, polar functional group that has not yet been added to peptoids but may demonstrate influence over peptoid conformation. In this research, peptoid monomers with varying alkyl side chain lengths were synthesized via solution-phase synthesis. Urea additions were then performed on these molecules and optimized for up to 100% conversion of starting material. In future work, we plan to purify these compounds for further analysis. Comparisons between NMR obtained via computational and real-world methods were also done in order to determine the relevance of computations for the creation of potential peptoid libraries.