Precise control over the composition, sequence and architecture of synthetic polymers is critical for mediating a high level of control over their chemical and physical attributes. Naturally occurring biomacromolecules including peptides, nucleic acids and oligosaccharides, have evolved over millennia to exhibit this level of control. However, synthetic analogs with comparable sequence and structural control remain scarce. Motivated by these opportunities and the need for sequence-control and structural diversity in polymer research, we present a versatile methodology for the synthesis of a new class of sequence-defined abiotic oligomers. Our approach to sequence-defined oligomer assembly involves the sequential and iterative addition of <i>N</i>-allylacrylamide and dithiol monomers to build sequence-defined oligothioetheramides (oligoTEAs) on a soluble fluorous support. The combination of fast solution-phase reaction kinetics with a robust fluorous solid-phase extraction (FSPE) technology allows for the efficient assembly of molecularly encoded synthetic oligoTEAs with broad structural diversity and tunability. Strategic placement of complementary reactive monomers during the oligoTEA assembly process facilitates the assembly of a wide variety of sequence-defined architectures. These novel sequences and structures will be presented and used to investigate the effect of primary sequence and structure on macromolecular and biological properties, including their use as potent antimicrobial agents and intracellular probes.

Synthesis and applications of bio-inspired oligoTEA peptidomimetics

254th National Meeting (2017)

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