Peptoids advance multidisciplinary research and undergraduate education in parallel: Sequence influences peptoid-lipid interactions

Peptoids are versatile peptidomimetic molecules with wide-ranging applications from drug discovery to materials science. An understanding of peptoid sequence features that contribute to their interactions with lipids will be advantageous to expand the functions of peptoids in these varied fields. Further, these topics capture the enthusiasm of undergraduate students who participate in the preparation and study of diverse peptoids in laboratory coursework and/or in faculty-led research. Here, we present the synthesis and study of 21 peptoids with varied functionality, including 19 tripeptoids and two longer oligomers. We monitored fluorescence spectra for ten of the tripeptoids and observed differences in spectral features correlated with peptoid flexibility and relative positioning of chromophores. Interactions of representative tripeptoids and two longer peptoids with sonicated glycerophospholipid vesicles were also evaluated using fluorescence spectroscopy, revealing an increase in emission intensity at the λmax in the presence of lipids. We also summarize here the advantages of engaging students in peptoid-based projects as an effective strategy to advance both research and undergraduate educational objectives in parallel.