Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 14, Issue 20, Pages 22781-22789Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.1c19692
Keywords
N-carboxyanhydride; NCA; polypeptoid; peptoid; N-substituted NCA; NNCA; sarcosine
Funding
- USA National Science Foundation [DMR-1848054, CHE1807651]
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This study presents a facile method for synthesizing polypeptoids via transition-metal-catalyzed controlled polymerization, yielding high-molecular-weight linear polypeptoids with predictable length and low dispersity. These materials are resistant to protease degradation and well-tolerated by human cells, showing promise for biomedical applications.
Peptoids have attracted attention for application in biomedicine due to their advantageous properties as compared to peptides. The structural analogues are typically resistant to protease degradation and offer improved biocompatibility. Chemical routes to an impressive variety of short-chain, low-molecular-weight peptoids are well-established. However, synthetic methods for well-defined, high-molecular-weight polypeptoids with side chain diversity are still in their infancy. Here, we report a facile method for synthesis of polypeptoids via transition-metal-catalyzed controlled, living polymerization of N-substituted N-carboxyanhydrides. Our method is amenable to hydrophilic and hydrophobic side chains and yields high-molecular-weight linear polypeptoids of predictable length and low dispersity. Further, the polymer end groups can be tuned for biological targeting, and polypeptide-polypeptoid hybrids are readily prepared in one pot. Our materials are indeed resistant to common proteases and are well-tolerated by human cells. Overall, this work represents a significant stride toward access to tunable polypeptoids.
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