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A cationic alternating copolymer composed of ornithine and glycine with an ordered sequence for enhanced bacterial activity
Polymer Engineering and Science ( IF 3.2 ) Pub Date : 2021-02-08 , DOI: 10.1002/pen.25657
Fuqiang Liu 1, 2 , Nan Ma 1 , Jun Liu 1 , Qiongqiong Zhu 1 , Ting Yue 1 , Junhui Ma 1, 2 , Yuan Wang 1 , Wei Qu 1 , Paul K. Chu 3 , Yan Tang 1 , Wei Zhang 1
Affiliation  

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. 1H 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.

中文翻译:

由鸟氨酸和甘氨酸组成的阳离子交替共聚物,具有增强细菌活性的有序序列

无序阳离子多肽的链和节很复杂,可能会产生意想不到的生物学活性。本文中,Ugi的4CC反应用于合成包含鸟氨酸和甘氨酸的阳离子交替共聚物(聚(Orn-Alter-Gly)),并增强了细菌的抵抗力。在此技术中,异氰酸钾,4-(N-羰基苄氧基氨基)-1-丁醛和1-(4-甲氧基苯基)乙胺在不使用催化剂的情况下一步反应生成MPE取代的聚(Orn-Alter-Gly),然后通过除去N-(1-对甲氧基苯乙基)(MPE)基团可得到聚(Orn-Alter-Gly)。1个1 H NMR,傅立叶变换红外光谱和自动氨基酸分析证实,鸟氨酸和甘氨酸在聚(Orn-alter-Gly)链中交替连接。MPE取代的聚(Orn-Alter-Gly)和聚(Orn-Alter-Gly)对金黄色葡萄球菌大肠杆菌肺炎克雷伯菌铜绿假单胞菌均具有出色的抗菌活性,并且具有出色的生物相容性。合成策略和材料提供了有关如何获得有序序列阳离子多肽的新信息。
更新日期:2021-02-08
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