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A cationic alternating copolymer composed of ornithine and glycine with an ordered sequence for enhanced bacterial activity
Author(s) -
Liu Fuqiang,
Ma Nan,
Liu Jun,
Zhu Qiongqiong,
Yue Ting,
Ma Junhui,
Wang Yuan,
Qu Wei,
Chu Paul K.,
Tang Yan,
Zhang Wei
Publication year - 2021
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.25657
Subject(s) - cationic polymerization , copolymer , escherichia coli , polymer chemistry , amino acid , stereochemistry , antibacterial activity , materials science , chemistry , combinatorial chemistry , organic chemistry , biochemistry , biology , bacteria , gene , polymer , genetics
The chains and segments of unordered cationic polypeptides are complex and may produce unexpected biological activities. Herein, the Ugi's 4CC reaction is adopted to synthesize a cationic alternating copolymer comprising ornithine and glycine (poly(Orn‐alter‐Gly)) with an ordered sequence for enhanced bacterial resistance. In this technique, potassium isocyanate, 4‐(N‐carbobenzyloxyamino)‐1‐butyraldehyde and 1‐(4‐Methoxyphenyl)ethylamine react to produce MPE‐substituted poly(Orn‐alter‐Gly) in one step without using a catalyst and then poly(Orn‐alter‐Gly) is obtained by removing the N‐(1‐p‐methoxyphenethyl) (MPE) group. 1 H NMR, Fourier transform infrared spectroscopy, and automatic amino acid analysis confirm that ornithine and glycine are linked alternately in the poly(Orn‐alter‐Gly) chains. Both MPE‐substituted poly(Orn‐alter‐Gly) and poly(Orn‐alter‐Gly) have excellent antibacterial activity against Staphylococcus aureus , Escherichia coli , Klebsiella pneumoniae , and Pseudomonas aeruginosa as well as excellent biocompatibility. The synthesis strategy and materials provide new information on how to obtain ordered sequence cationic polypeptides.