Accelerated polymerization of N-carboxyanhydrides catalyzed by crown ether

Yingchun Xia, Ziyuan Song, Zhengzhong Tan, Tianrui Xue, Shiqi Wei, Lingyang Zhu, Yingfeng Yang, Hailin Fu, Yunjiang Jiang, Yao Lin, Yanbing Lu (), Andrew L. Ferguson () and Jianjun Cheng ()
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Yingchun Xia: University of Illinois at Urbana-Champaign
Ziyuan Song: University of Illinois at Urbana-Champaign
Zhengzhong Tan: University of Illinois at Urbana-Champaign
Tianrui Xue: University of Illinois at Urbana-Champaign
Shiqi Wei: University of Illinois at Urbana-Champaign
Lingyang Zhu: University of Illinois at Urbana-Champaign
Yingfeng Yang: University of Illinois at Urbana-Champaign
Hailin Fu: University of Connecticut
Yunjiang Jiang: University of Illinois at Urbana-Champaign
Yao Lin: University of Connecticut
Yanbing Lu: Hunan University
Andrew L. Ferguson: University of Chicago
Jianjun Cheng: University of Illinois at Urbana-Champaign

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract The recent advances in accelerated polymerization of N-carboxyanhydrides (NCAs) enriched the toolbox to prepare well-defined polypeptide materials. Herein we report the use of crown ether (CE) to catalyze the polymerization of NCA initiated by conventional primary amine initiators in solvents with low polarity and low hydrogen-bonding ability. The cyclic structure of the CE played a crucial role in the catalysis, with 18-crown-6 enabling the fastest polymerization kinetics. The fast polymerization kinetics outpaced common side reactions, enabling the preparation of well-defined polypeptides using an α-helical macroinitiator. Experimental results as well as the simulation methods suggested that CE changed the binding geometry between NCA and propagating amino chain-end, which promoted the molecular interactions and lowered the activation energy for ring-opening reactions of NCAs. This work not only provides an efficient strategy to prepare well-defined polypeptides with functionalized C-termini, but also guides the design of catalysts for NCA polymerization.

Date: 2021
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DOI: 10.1038/s41467-020-20724-w

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