Synthesis of Single-Ring Nanoparticles Mimicking Natural Cyclotides by a Stepwise Folding-Activation-Collapse Process

Macromolecular Rapid Communications
Jon Rubio-CervillaJosé A Pomposo

Abstract

Cyclotides are small cyclic polypeptides found in a variety of organisms, ranging from bacteria to plants. Their ring structure endows those polypeptides with specific properties, such as improved stability against enzymatic degradation. Optimal cyclotide activity is often observed only in the presence of intra-ring disulfide bonds. Synthesis of soft nano-objects mimicking the conformation of natural cyclotides remains challenging. Here, a new class of natural cyclotide mimics synthesized by a stepwise folding-activation-collapse process at high dilution starting from simple synthetic precursor polymers is established. The initial folding step is carried out by a photoactivated hetero Diels-Alder (HDA) ring-closing reaction, which is accompanied by chain compaction of the individual precursor polymer chains as determined by size exclusion chromatography (SEC). The subsequent activation step comprises a simple azidation procedure, whereas the final collapse step is driven by CuAAC in the presence of an external cross-linker, providing additional compaction to the final single-ring nanoparticles (SRNPs). The unique structure and compaction degree of the SRNPs is established via a detailed comparison with conventional single-chain...Continue Reading

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Citations

Oct 22, 2019·Macromolecular Rapid Communications·Steve NeumannWolfgang H Binder
Sep 12, 2019·Macromolecular Rapid Communications·Hendrik FrischChristopher Barner-Kowollik
Apr 18, 2021·Macromolecular Rapid Communications·Meshari A M AlqarniC Remzi Becer
Apr 25, 2019·Journal of the American Chemical Society·Avishai LevyCharles E Diesendruck

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