Superfast and Water-Insensitive Polymerization on α-Amino Acid N-Carboxyanhydrides to Prepare Polypeptides Using Tetraalkylammonium Carboxylate as the Initiator

Yueming Wu; Kang Chen; Xue Wu; Longqiang Liu; Weiwei Zhang; Yun Ding; Shiqi Liu; Min Zhou; Ning Shao; Zhemin Ji; Jiacheng Chen; Minghui Zhu; Runhui Liu

doi:10.1002/anie.202103540

Superfast and Water-Insensitive Polymerization on α-Amino Acid N-Carboxyanhydrides to Prepare Polypeptides Using Tetraalkylammonium Carboxylate as the Initiator

Angew Chem Int Ed Engl. 2021 Dec 6;60(50):26063-26071. doi: 10.1002/anie.202103540. Epub 2021 Nov 9.

Authors

Yueming Wu¹, Kang Chen², Xue Wu², Longqiang Liu², Weiwei Zhang², Yun Ding³, Shiqi Liu², Min Zhou², Ning Shao², Zhemin Ji², Jiacheng Chen⁴, Minghui Zhu⁴, Runhui Liu^{1

2}

Affiliations

¹ State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200237, China.
² Key Laboratory for Ultrafine Materials of Ministry of Education, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Research Center for Biomedical Materials of Ministry of Education, East China University of Science and Technology, Shanghai, 200237, China.
³ Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai, 200237, China.
⁴ School of Chemical Engineering, East China University of Science and Technology, Shanghai, 200237, China.

PMID: 34569145
DOI: 10.1002/anie.202103540

Abstract

We design the tetraalkylammonium carboxylate-initiated superfast polymerization on α-amino acid N-carboxyanhydrides (NCA) for efficient synthesis of polypeptides. Carboxylates, as a new class of initiator for NCA polymerization, can initiate the superfast NCA polymerization without the need of extra catalysts and the polymerization can be operated in open vessels at ambient condition without the use of glove box. Tetraalkylammonium carboxylate-initiated polymerization on NCA easily affords block copolymers with at least 15 blocks. Moreover, this method avoids tedious purification steps and enables direct polymerization on crude NCAs in aqueous environments to prepare polypeptides and one-pot synthesis of polypeptide nanoparticles. These advantages and the mild polymerization condition of tetraalkylammonium carboxylate-initiated NCA polymerization imply its great potential in functional exploration and application of polypeptides.

Keywords: NCA polymerization; antimicrobial; aqueous polymerization; in situ self-assembly; tetraalkylammonium carboxylate.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding