Issue 11, 2021

Open-air synthesis of oligo(ethylene glycol)-functionalized polypeptides from non-purified N-carboxyanhydrides

Abstract

With PEG-like properties, such as hydrophilicity and stealth effect against protein absorption, oligo(ethylene glycol) (OEG)-functionalized polypeptides have emerged as a new class of biomaterials alternative to PEG with polypeptide-like properties. Synthesis of this class of materials, however, has been demonstrated very challenging, as the synthesis and purification of OEG-functionalized N-carboxyanhydrides (OEG-NCAs) in high purity, which is critical for the success in polymerization, is tedious and often results in low yield. OEG-functionalized polypeptides are therefore only accessible to a few limited labs with expertise in this specialized NCA chemistry and materials. Here, we report the controlled synthesis of OEG-functionalized polypeptides in high yield directly from the OEG-functionalized amino acids via easy and reproducible polymerization of non-purified OEG-NCAs. The prepared amphiphilic block copolypeptides can self-assemble into narrowly dispersed nanoparticles in water, which show properties suitable for drug delivery applications.

Graphical abstract: Open-air synthesis of oligo(ethylene glycol)-functionalized polypeptides from non-purified N-carboxyanhydrides

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2021
Accepted
07 Apr 2021
First published
30 Apr 2021

Biomater. Sci., 2021,9, 4120-4126

Open-air synthesis of oligo(ethylene glycol)-functionalized polypeptides from non-purified N-carboxyanhydrides

Z. Tan, Z. Song, T. Xue, L. Zheng, L. Jiang, Y. Jiang, Z. Fu, A. Nguyen, C. Leal and J. Cheng, Biomater. Sci., 2021, 9, 4120 DOI: 10.1039/D1BM00223F

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