Poly-N-substituted glycine peptides (peptoids) are non-natural synthetic polymers that are based on a peptide polyglycine backbone with side chain substitutions on the amide nitrogen rather than the a-carbon, leading to novel physical and chemical properties. In the past we have developed several peptoids designed for grafting onto surfaces where they confer resistance to fouling by proteins, cells and bacteria. In this talk we will describe two peptoid variations inspired by the most effective antifouling molecules in nature: the glycocalyx and zwitterions. The precise sequence specificity afforded by solid phase synthesis allowed us to probe several molecular designs in which the placement of mono- and disaccharides is varied. In the case of zwitterionic peptoids, the effect of charge separation on protein fouling resistance was emphasized. Results of protein and cell fouling studies of these surface grafted peptoid systems were coupled with computational studies using molecular dynamics and molecular theory, providing insight into important molecular features of antifouling peptoids and guiding the design and optimization of these systems for optimal performance.

Novel zwitterionic and glycopeptoids and their applications at the biointerface

248th National Meeting (2014)

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