多酚氧化酶对蚕丝及丝蛋白生物材料的改性与应用研究进展
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摘要
多酚氧化酶能催化氧化酚类结构生成醌类活性中间体,引发酚类单体之间聚合。家蚕丝素蛋白和丝胶蛋白大分子肽链上均含一定数量的酪氨酸残基,酪氨酸的酚羟基能被多酚氧化酶催化氧化,生成醌类活性基,不仅可促成丝蛋白大分子交联,而且可与外源氨基功能化合物发生迈克尔加成或席夫碱反应,实现底物分子改造。本文讨论了多酚氧化酶的催化氧化机制,侧重阐述了近年来国内外应用多酚氧化酶(漆酶和酪氨酸酶)进行丝蛋白生物材料加工的研究,包括丝纤维制品酶法抗菌和防皱整理、丝素或丝胶酶促交联与接枝改性、再生丝蛋白膜及功能性生物材料制备等,为蚕丝及丝蛋白基材料的生物改性研究及开发利用提供参考。
Polyphenol oxidase(PPO) can catalyze the oxidation of phenolic groups to form reactive quinone intermediates, and initiate the polymerization of the phenolic monomers. The macromolecular peptide chains in silk fibroin and sericin contain a certain number of tyrosine residues, whose phenolic hydroxyl group can be oxidized by polyphenol oxidase to produce quinone groups. These active groups might result in self-crosslinking of the macromolecules of silk proteins, and react with the amino functional compounds simultaneously to transform substrate molecule via Michael addition reaction or Schiff base reactions. In this paper, the catalytic oxidation mechanisms of polyphenol oxidases were discussed, meanwhile, researches at home and abroad on the processing of silk-based biomaterials with polyphenol oxidases(laccase and tyrosinase) were introduced, including enzymatic anti-microbial finishing and anti-crease finishing of silk textiles, enzymatic crosslinking and grafting of silk fibroin and sericin proteins, preparation of regenerated silk protein films and functional biomaterials. These studies will facilitate the study on bio-modification of silk fibers and silk-based materials and their future utilization.
Polyphenol oxidase(PPO) can catalyze the oxidation of phenolic groups to form reactive quinone intermediates, and initiate the polymerization of the phenolic monomers. The macromolecular peptide chains in silk fibroin and sericin contain a certain number of tyrosine residues, whose phenolic hydroxyl group can be oxidized by polyphenol oxidase to produce quinone groups. These active groups might result in self-crosslinking of the macromolecules of silk proteins, and react with the amino functional compounds simultaneously to transform substrate molecule via Michael addition reaction or Schiff base reactions. In this paper, the catalytic oxidation mechanisms of polyphenol oxidases were discussed, meanwhile, researches at home and abroad on the processing of silk-based biomaterials with polyphenol oxidases(laccase and tyrosinase) were introduced, including enzymatic anti-microbial finishing and anti-crease finishing of silk textiles, enzymatic crosslinking and grafting of silk fibroin and sericin proteins, preparation of regenerated silk protein films and functional biomaterials. These studies will facilitate the study on bio-modification of silk fibers and silk-based materials and their future utilization.
引文
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[12] HONG Y Q,ZHU X K,WANG P,et al.Tyrosinase-mediated construction of a silk fibroin/elastin nanofiber bioscaffold[J].Appl Biochem Biotechnol,2016,178(7):1363-1376
[13] 李新玥,邢铁玲.基于酪氨酸酶的丝素蛋白膜的制备及其性能[J].丝绸,2013,50(10):24-29
[14] ZHANG Q,CUI L,WANG P,et al.Improving properties of silk sericin membranes via enzymatic oxidation with laccase and TEMPO[J].Biotechnol Appl Biochem,2017,65:372-380
[15] 张谦.基于漆酶/TEMPO催化的丝胶蛋白改性及再生材料构建 [D].无锡:江南大学,2017
[16] ZHOU Q,ZHANG Q,WANG P,et al.Enhancement biocompatibility of bacterial cellulose membrane via laccase/TEMPO mediated grafting of silk fibroins[J].Fibers Polym,2017,18(8):1478-1485
[17] 郭守娇,杨慕莹,邢铁玲,等.漆酶催化ε-聚赖氨酸接枝蚕丝织物的抗皱整理工艺优化试验[J].蚕业科学,2012,38(6):1044-1050
[18] WANG P,YUAN M L,CUI L,et al.Modification of Bombyx mori silk fabrics by tyrosinase-catalyzed grafting of chitosan[J].Eng Life Sci,2014,14(2):211-217
[19] WANG P,ZHOU Y,CUI L,et al.Enzymatic grafting of lactoferrin onto silk fibroins for antibacterial functionalization[J].Fibers Polym,2014,15(10):2045-2050
[20] XING T,LI X,GUO S,et al.Preparation and properties of silk fabric grafted with-polylysine by tyrosinase[J].Text Res J,2015,85(16):1743-1748
[21] 王平,邱华,成钢,等.一种生物酶法真丝织物阻燃整理方法:201210318957.1[P].2016-04-13
[22] 齐成龙.基于酶促改性的抗氧化丝素膜的制备[D].无锡:江南大学,2015
[23] FREDDI G,ANGHILERI A,SAMPAIO S,et al.Tyrosinase cata-lyzed modification of Bombyx mori silk fibroin:grafting of chitosan under heterogeneous reaction conditions[J].J Biotechnol,2006,125(2):281-294
[24] MONTI P,FREDDI G,SAMPAIO S,et al.Structure modifications induced in silk fibroin by enzymatic treatments:a Raman study[J].J Mol Struct,2005,744:685-690
[25] KANG G D,LEE K H,CHANG S K,et al.Crosslinking reaction of phenolic side chains in silk fibroin by tyrosinase[J].Fibers Polym,2004,5(3):234-238
[26] SAMPAIO S,TADDEI P,MONTI P,et al.Enzymatic grafting of chitosan onto Bombyx mori silk fibroin:kinetic and IR vibrational studies[J].J Biotechnol,2005,116(1):21-33
[27] ZHU X K,WANG P,CUI L,et al.Enhancement reactivity of Bombyx mori silk fibroins via genipin-mediated grafting of a tyrosine-rich polypeptide[J].J Text Inst,2017,108(12):2115-2122
[28] WANG P,ZHU X K,YUAN J G,et al.Grafting of tyrosine-containing peptide onto silk fibroin membrane for improving enzymatic reactivity[J].Fibers Polym,2016,17(9):1323-1329
[2] TORRES E,BUSTOS I,BORGNE S L.Potential use of oxidative enzymes for the detoxification of organic pollutants[J].Appl Catal,B,2003,46(1):1-15
[3] BRUYNEEL F,ENAUDE,BILLOTTET L,et al.Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase[J].Eur J Org Chem,2010,2008(1):72-79
[4] NAGAI M,SATO T,WATANABE H,et al.Purification and characterization of an extracellular laccase from the edible mushroom Lentinula edodes,and decolorization of chemically different dyes[J].Appl Microbiol Biotechnol,2002,60(3):327-335
[5] ABADULLA E,TZANOV T,CASTA S,et al.Decolorization and detoxification of textile dyes with a laccase from Trametes hirsuta[J].Appl Environ Microbiol,2000,66(8):3357-3362
[6] RAJAGURU P,KALAISELV K,PALANIVEL M,et al.Biodegradation of azo dyes in a sequential anaerobic-aerobic system[J].Appl Microbiol Biotechnol,2000,54(2):268-273
[7] FACCIO G,KRUUS K,SALOHEIMO M,et al.Bacterial tyrosinases and their applications[J].Process Biochem,2012,47(12):1749-1760
[8] 欧志敏,王普,王鸿,等.酪氨酸酶的应用研究进展[J].中国生物工程杂志,2005(增刊):163-169
[9] 张廷红,葛长海,万海清.酪氨酸酶的应用研究进展[J].沿海企业与科技,2005(2):161-163
[10] QI C L,WANG P,CUI L,et al.Enhancement of antioxidant ability of Bombyx mori silk fibroins by enzymatic coupling of catechin[J].Appl Microbiol Biotechnol,2016,100(4):1713-1722
[11] 袁萌莉.羊毛织物生物酶同浴染色与功能改性[D].无锡:江南大学,2016
[12] HONG Y Q,ZHU X K,WANG P,et al.Tyrosinase-mediated construction of a silk fibroin/elastin nanofiber bioscaffold[J].Appl Biochem Biotechnol,2016,178(7):1363-1376
[13] 李新玥,邢铁玲.基于酪氨酸酶的丝素蛋白膜的制备及其性能[J].丝绸,2013,50(10):24-29
[14] ZHANG Q,CUI L,WANG P,et al.Improving properties of silk sericin membranes via enzymatic oxidation with laccase and TEMPO[J].Biotechnol Appl Biochem,2017,65:372-380
[15] 张谦.基于漆酶/TEMPO催化的丝胶蛋白改性及再生材料构建 [D].无锡:江南大学,2017
[16] ZHOU Q,ZHANG Q,WANG P,et al.Enhancement biocompatibility of bacterial cellulose membrane via laccase/TEMPO mediated grafting of silk fibroins[J].Fibers Polym,2017,18(8):1478-1485
[17] 郭守娇,杨慕莹,邢铁玲,等.漆酶催化ε-聚赖氨酸接枝蚕丝织物的抗皱整理工艺优化试验[J].蚕业科学,2012,38(6):1044-1050
[18] WANG P,YUAN M L,CUI L,et al.Modification of Bombyx mori silk fabrics by tyrosinase-catalyzed grafting of chitosan[J].Eng Life Sci,2014,14(2):211-217
[19] WANG P,ZHOU Y,CUI L,et al.Enzymatic grafting of lactoferrin onto silk fibroins for antibacterial functionalization[J].Fibers Polym,2014,15(10):2045-2050
[20] XING T,LI X,GUO S,et al.Preparation and properties of silk fabric grafted with-polylysine by tyrosinase[J].Text Res J,2015,85(16):1743-1748
[21] 王平,邱华,成钢,等.一种生物酶法真丝织物阻燃整理方法:201210318957.1[P].2016-04-13
[22] 齐成龙.基于酶促改性的抗氧化丝素膜的制备[D].无锡:江南大学,2015
[23] FREDDI G,ANGHILERI A,SAMPAIO S,et al.Tyrosinase cata-lyzed modification of Bombyx mori silk fibroin:grafting of chitosan under heterogeneous reaction conditions[J].J Biotechnol,2006,125(2):281-294
[24] MONTI P,FREDDI G,SAMPAIO S,et al.Structure modifications induced in silk fibroin by enzymatic treatments:a Raman study[J].J Mol Struct,2005,744:685-690
[25] KANG G D,LEE K H,CHANG S K,et al.Crosslinking reaction of phenolic side chains in silk fibroin by tyrosinase[J].Fibers Polym,2004,5(3):234-238
[26] SAMPAIO S,TADDEI P,MONTI P,et al.Enzymatic grafting of chitosan onto Bombyx mori silk fibroin:kinetic and IR vibrational studies[J].J Biotechnol,2005,116(1):21-33
[27] ZHU X K,WANG P,CUI L,et al.Enhancement reactivity of Bombyx mori silk fibroins via genipin-mediated grafting of a tyrosine-rich polypeptide[J].J Text Inst,2017,108(12):2115-2122
[28] WANG P,ZHU X K,YUAN J G,et al.Grafting of tyrosine-containing peptide onto silk fibroin membrane for improving enzymatic reactivity[J].Fibers Polym,2016,17(9):1323-1329