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 -substituted -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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acsami.1c19692 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A modular and extensible CHARMM-compatible model for all-atom simulation of polypeptoids.
J Chem Phys
December 2024
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, USA.
Peptoids (N-substituted glycines) are a class of sequence-defined synthetic peptidomimetic polymers with applications including drug delivery, catalysis, and biomimicry. Classical molecular simulations have been used to predict and understand the conformational dynamics of single chains and their self-assembly into morphologies including sheets, tubes, spheres, and fibrils. The CGenFF-NTOID model based on the CHARMM General Force Field has demonstrated success in accurate all-atom molecular modeling of peptoid structure and thermodynamics.
View Article and Find Full Text PDFEasy access to amphiphilic nitrogenous block copolymers switchable catalysis.
Chem Sci
October 2024
Department of Polymeric Materials, School of Materials Science and Engineering, Tongji University 4800 Caoan Road Shanghai 201804 China
A key challenge in polymer synthesis is to develop new methods that enable block copolymers to be prepared from mixed monomer feedstock. The emerging switchable polymerization catalysis can generate block copolymers with well-defined structures and tunable properties from monomer mixtures. However, constrained by the reactivity of monomers and the incompatibility of different polymerization mechanisms, this method is usually confined to oxygenated monomers.
View Article and Find Full Text PDFSelf-promoted Controlled Ring-opening Polymerization via Side Chain-mediated Proton Transfer for the Synthesis of Tertiary Amine-pendant Polypeptoids.
Angew Chem Int Ed Engl
October 2024
State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Jiangsu Key Laboratory of Advanced Functional Polymer Materials, Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China.
Proton transfer is essential in virtually all biochemical processes, with enzymes facilitating this transfer by optimizing the proximity and orientation of reactants through site-specific hydrogen bonds. Proton transfer is also crucial in the rate-determining step for the ring-opening polymerization of N-carboxyanhydrides (NCAs), widely used to prepare various peptidomimetic materials. This study utilizes side chain-assisted strategy to accelerate the rate of chain propagation by using NCAs with tertiary amine pendants.
View Article and Find Full Text PDFCrystallization ripening and erosion of calcium oxalate under the effect of bacteria and a polymer materials surface.
J Mater Chem B
October 2024
Jiangsu Key Laboratory of Neuropsychiatric Diseases, Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development, and College of Pharmaceutical Sciences, Soochow University, Suzhou, 215123, China.
As typical examples of pathological biomineralization, urinary stones and stent encrustation have been associated with bacteria, yet the underlying mechanisms remain unclear. In this study, the effect of Gram-negative and Gram-positive on the nucleation and growth of calcium oxalate crystals both in solution and on material surfaces was investigated. Both bacteria can promote calcium oxalate crystallization, and shows a prominent ability to boost the nucleation and growth rate.
View Article and Find Full Text PDFEvaluating Cryo-TEM Reconstruction Accuracy of Self-Assembled Polymer Nanostructures.
Macromol Rapid Commun
January 2025
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA, 94720, USA.
Cryogenic transmission electron microscopy (cryo-TEM) combined with single particle analysis (SPA) is an emerging imaging approach for soft materials. However, the accuracy of SPA-reconstructed nanostructures, particularly those formed by synthetic polymers, remains uncertain due to potential packing heterogeneity of the nanostructures. In this study, the combination of molecular dynamics (MD) simulations and image simulations is utilized to validate the accuracy of cryo-TEM 3D reconstructions of self-assembled polypeptoid fibril nanostructures.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!