Molecular Engineering of Peptoid Scaffolds for Spatial Display of Functional Groups: Siderophore-Mimic Peptoids and Pigment-Displaying Peptoids

Abstract

This thesis explores the versatile applications of peptoids due to their tunable side chains and well-defined secondary structures. It consists of four studies, each presented in separate chapters. Chapter 1 serves as an introduction. Chapters 2 and 3 develop design principles for siderophore-inspired compounds and their applications in antibacterial therapy. Chapter 2 details novel cyclic peptoids with catechol moieties mimicking natural siderophores' iron-binding, which forms stable tris(catecholato) iron(III) complexes. Conjugated with antibiotics, these compounds showed significant activity against drug-resistant Acinetobacter baumannii. Chapter 4 incorporates chiral submonomers into peptoids, producing helices with circularly polarized luminescence through controlled backbone homogeneity. Chapter 5 uses peptoids to precisely arrange donor-acceptor pigments for studying electron transfer kinetics, revealing improved electron transfer with an anthracene/DMA pair. These findings highlight peptoids’ potential in developing antibacterial agents and optically active materials.