Issue 3, 2022

Facile synthesis of polypeptoids bearing bulky sidechains via urea accelerated ring-opening polymerization of α-amino acid N-substituted N-carboxyanhydrides

Abstract

Polypeptoids, as synthetic mimics of polypeptides, exhibit a variety of biological functions and excellent proteolytic stability. Polypeptoids can be synthesized by the ring-opening polymerization of α-amino acid N-substituted N-carboxyanhydrides (NNCAs); however, they suffer from the generally slow reactivity and poor stability of NNCAs, especially those with bulky substitutes. This long-standing challenge greatly limits the synthesis of polypeptoids with diverse structures. Herein, we found that commercially available 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea can greatly accelerate the primary amine-initiated ring-opening polymerization of NNCAs by activating the NNCA carbonyl via hydrogen bonding interactions. Urea-catalyzed NNCA polymerization is compatible with diverse NNCAs in preparing polypeptoids with variable polymer lengths and narrow dispersity and is especially suitable for inactive NNCAs bearing bulky N-substitutes, such as cyclohexyl-NNCA. This urea-catalyzed NNCA polymerization strategy will substantially increase the structural diversity and functional study of polypeptoids, implying wider and diverse applications of these polypeptide mimics.

Graphical abstract: Facile synthesis of polypeptoids bearing bulky sidechains via urea accelerated ring-opening polymerization of α-amino acid N-substituted N-carboxyanhydrides

Supplementary files

Article information

Article type
Paper
Submitted
02 Okt 2021
Accepted
06 Dis 2021
First published
07 Dis 2021

Polym. Chem., 2022,13, 420-426

Facile synthesis of polypeptoids bearing bulky sidechains via urea accelerated ring-opening polymerization of α-amino acid N-substituted N-carboxyanhydrides

K. Chen, Y. Wu, X. Wu, M. Zhou, R. Zhou, J. Wang, X. Xiao, Y. Yuan and R. Liu, Polym. Chem., 2022, 13, 420 DOI: 10.1039/D1PY01324F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements