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Water‐Insensitive Synthesis of Poly‐β‐Peptides with Defined Architecture
Author(s) -
Zhou Min,
Xiao Ximian,
Cong Zihao,
Wu Yueming,
Zhang Wenjing,
Ma Pengcheng,
Chen Sheng,
Zhang Haodong,
Zhang Danfeng,
Zhang Donghui,
Luan Xiangfeng,
Mai Yiyong,
Liu Runhui
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202001697
Subject(s) - polymerization , copolymer , chemistry , peptide , combinatorial chemistry , polymer chemistry , dispersity , fluorophore , ring opening polymerization , organic chemistry , polymer , biochemistry , fluorescence , physics , quantum mechanics
Biocompatible and proteolysis‐resistant poly‐β‐peptides have broad applications and are dominantly synthesized via the harsh and water‐sensitive ring‐opening polymerization of β‐lactams in a glovebox or using a Schlenk line, catalyzed by the strong base LiN(SiMe 3 ) 2 . We have developed a controllable and water‐insensitive ring‐opening polymerization of β‐amino acid N‐thiocarboxyanhydrides (β‐NTAs) that can be operated in open vessels to prepare poly‐β‐peptides in high yields, with diverse functional groups, variable chain length, narrow dispersity and defined architecture. These merits imply wide applications of β‐NTA polymerization and resulting poly‐β‐peptides, which is validated by the finding of a HDP‐mimicking poly‐β‐peptide with potent antimicrobial activities. The living β‐NTA polymerization enables the controllable synthesis of random, block copolymers and easy tuning of both terminal groups of polypeptides, which facilitated the unravelling of the antibacterial mechanism using the fluorophore‐labelled poly‐β‐peptide.