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化学进展 2022, Vol. 34 Issue (8): 1796-1808 DOI: 10.7536/PC211009 前一篇   后一篇

• 综述 •

酶催化原子转移自由基聚合

王慧悦1, 胡欣2,*(), 胡玉静1,*(), 朱宁1,*(), 郭凯1   

  1. 1 南京工业大学生物与制药工程学院 材料化学工程国家重点实验室 南京 211800
    2 南京工业大学材料科学与工程学院 南京 211800
  • 收稿日期:2021-10-11 修回日期:2021-12-23 出版日期:2022-08-20 发布日期:2022-04-01
  • 通讯作者: 胡欣, 胡玉静, 朱宁
  • 基金资助:
    国家重点研发计划(2019YFA0905000); 国家自然科学基金(21604037); 江苏省先进生物制造创新中心项目(XTD1823); 江苏省先进生物制造创新中心项目(XTB1802)
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Enzyme-Catalyzed Atom Transfer Radical Polymerization

Huiyue Wang1, Xin Hu2(), Yujing Hu1(), Ning Zhu1(), Kai Guo1   

  1. 1 College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University,Nanjing 211800, China
    2 College of Materials Science and Engineering, Nanjing Tech University, Nanjing 211800, China
  • Received:2021-10-11 Revised:2021-12-23 Online:2022-08-20 Published:2022-04-01
  • Contact: Xin Hu, Yujing Hu, Ning Zhu
  • Supported by:
    National Key R&D Program of China(2019YFA0905000); National Natural Science Foundation of China(21604037); Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture(XTD1823); Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture(XTB1802)

原子转移自由基聚合(ATRP)是制备分子量以及分散度可控聚合物的重要途径。然而,受制于除氧步骤复杂、金属催化剂残留以及单体适用范围有限等因素,ATRP难以应用于批量制备功能化聚合物/共聚物材料,限制了其进一步应用。近年来提出和发展的酶催化聚合,为高效便捷除氧、拓展单体适用范围以及制备具有特殊(纳米)结构的纯净聚合物/共聚物提供了新思路。本文详细介绍了酶的结构与催化机理,以酶的种类进行分类,系统总结了具有不同结构的酶催化体系(包括过氧化辣根酶、血红蛋白、血红素、漆酶等)的催化机理、适用单体、优缺点及应用等;综述了酶以及酶模拟物催化ATRP体系的发展现状;最后,对酶催化ATRP的发展前景和挑战进行了探讨和展望。

关键词： 原子转移自由基聚合, 酶, 催化

Atom transfer radical polymerization (ATRP) is an important method for preparing polymers with controllable molecular weight and polydispersity. However, due to the complex oxygen removal steps, metal catalysts residue, and limited monomer scope, it is difficult for ATRP to be widely used in the large-scale preparation of functionalized polymers/copolymers. With the development of enzyme-catalyzed polymerization, radical polymerization has made significant progress in efficient and convenient oxygen removal, expanding monomer scope, and the synthesis of polymers/copolymers with special (nano) structures. This review highlights the structure of enzymes and their catalytic mechanism in enzyme-catalyzed ATRP. Various enzyme/ enzyme mimics catalysis system (including horseradish peroxidase, hemoglobin, heme, laccase, etc.) employed in ATRP are carefully summarized in order. Finally, the opportunities and challenges of enzyme-catalyzed ATRP are discussed for the further development in this field.

Enzyme-Catalyzed Atom Transfer Radical Polymerization

Contents

1 Introduction

2 Horseradish peroxidase (HRP) catalyzed ATRP

3 Hemoglobin catalyzed ATRP

4 Hemin and Enzyme mimic catalyzed ATRP

5 Laccase catalyzed ATRP

6 GOx-HRP cascade catalysis applied as initiator

7 Conclusion and outlook

Key words: ATRP, enzyme, catalysis
()
表1 不同酶催化乙烯基单体的ATRP聚合
Table 1 Different enzymes catalyze the polymerization of vinyl monomers by ATRP Table Reviews
Active center Catalyst Monomers Mn (g/mol) Conversion (%) -D ref
Fe HRP NIPAAm 50,000~220,000 38 1.40~1.80 67
HRP(immobiile) PEGA 3000 40 1.55 68
HRP(free) PEGA 3,400 12 1.18 69
HRP-THS PEGA 4,400 6 1.08 69
HRP(free) PEGA 43,700 18 1.23 69
HRP/GOx/Cu(ppm) OEOMA500 70,000 79~94 1.13~1.27 106
Hb NIPAAm / / uncontrollable 75
Hb PPEGA 6,200~6,500 58 1.42 75
Hb PPEGMA 6,200~6,500 63 ≤1.17 75
hydroxyhemin NIPAAm 22,700 80 1.80 80
Mesohemin MPEG550 10,300 39 1.55 81
DhHP-6@ZIF-8 PEGMA500 45,900 76 1.27 82
catalase PEGA 8,700 90 ≤1.7 46
Cu laccase PEGMA 17,100 28 1.94 45
laccase NVIm 5,100 70 1.56 91
Copper chlorophyllin PEGA 4,000~5,000 16 ≤1.11 94
图式1 (a) 辣根过氧化物酶结构; (b) HRP的催化机理示意图[66]
Scheme 1 (a) The Structure of Horseradish Peroxidase. (b) Schematic diagram of HRP catalytic mechanism[66]
图式2 ARGET ATRP条件下的HRP催化机理[67]
Scheme 2 Putative mechanism of HRP-catalyzed polymerization under ARGET ATRP condition[67]
图1 通过生物催化ATRP用聚合物填充聚合物囊泡[68]
Fig. 1 Filling of polymersomes with polymers by biocatalytic ATRP[68]
图式3 通过ATRPase合成的用于体内ROS响应生物荧光成像的MPG示意图。(a) 制备SiO2@MPGs。(b) 串联催化SiO2@MPGs响应荧光成像的机理图[70]
Scheme 3 Schematic illustration of the MPGs synthesized by ATRPase for ROS responsive biofluorescence imaging in vivo. (a) Preparation of MPGs encapsulating SiO2@MPGs. (b) Mechanism illustration of ROS responsive fluorescence imaging by tandem catalysis with SiO2@MPGs[70]
图式4 血红蛋白催化ARGET ATRP的预测机理[75]
Scheme 4 Possible mechanism of Hb-Catalyzed Polymerization under ARGET ATRP Conditions[75]
图式5 NIPAM的多步SI-ATRP示意图[76]
Scheme 5 Schematic Representation of Multistep SI-ATRP of NIPAM[76]
图2 以GCE/PTB/nPt为阴极,通过eATRP合成PIP[78]
Fig. 2 Synthesis scheme of PIPs via eATRP with GCE/PTB/nPt as cathode[78]
图式6 羟高铁血红素的化学结构[80]
Scheme 6 Chemical structure of hydroxyhemin[80]
图式7 血红素催化聚合NIPAAm的预测机理[80]
Scheme 7 Proposed mechanism for polymerization of NIPAAm catalyzed by hematin[80]
图式8 (a)水相溶液中MAA的ATRP聚合;(b)中亚血红素-(MPEG550)2催化剂的结构;(c)三种引发剂的结构[81]
Scheme 8 (a) ATRP of MAA in aqueous solution; (b) Mesohemin-(MPEG550)2 catalyst; (c) Structure of polymerization Initiators[81]
图式9 (a) DhHP-6的结构;(b) DhHP-6催化PEGMA500的ARGET ATRP聚合[82]
Scheme 9 (a) Structure of DhHP-6; (b) DhHP-6 catalyzed ARGET ATRP of PEGMA500[82]
图3 DhHP-6@ZIF-8催化合成PEGMA500的ATRP机理[83]
Fig. 3 Detailed mechanism of DhHP-6@ZIF-8-induced ATRP reaction of PEGMA500[83]
图式10 (a) 漆酶活性位点的示意图; (b) 漆酶和烷基卤化物的激活/失活机理[45]
Scheme 10 (a) Schematic representation of the active site of laccase. (b) Possible activation/deactivation mechanism involving laccase from T. versicolor and alkyl halides[45]
图式11 在不同配体存在下,酶促ARGET ATRP合成聚(PEGA480)[92]
Scheme 11 Synthesis of poly(PEGA480) by enzymatic ARGET ATRP in the presence of different ligands[92]
图式12 漆酶-聚合物共聚物的合成与表征[93]。
Scheme 12 Synthesis and characterization of laccase-polymer biohybrids[93]
图式13 叶绿素铜催化的电子转移ATRP(AGET ATRP)生成的活化剂的可能机理及和二氢卟酚结构[94]
Scheme 13 Proposed mechanism for activator generated by electron transfer ATRP (AGET ATRP) catalyzed by copper chlorophyllin and structure of the chlorins[94]
图式14 “消耗氧气”的ATRP聚合过程[106]
Scheme 14 Overall process of “oxygen-fueled” ATRP[106]
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摘要

酶催化原子转移自由基聚合