One-Enzyme Triple Catalysis: Employing the Promiscuity of Horseradish Peroxidase for Synthesis and Functionalization of Well-Defined Polymers

ACS Macro Letters

Volumn 7, Issue 1, 2018, Pages 1-6

  Liu, Zhifen ^a   Lv, Yue ^a   Zhu, Anqi ^a   An, Zesheng ^a  

^a SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FOOD PRODUCTS; LIVING POLYMERIZATION;

CATALYTIC REACTIONS; DIELS-ALDER REACTION; FUNCTIONALIZATIONS; HORSE-RADISH PEROXIDASE; POLYMER CHEMISTRY; RAFT POLYMERIZATION; THIOL-ENES;

ENZYMES;

EID: 85040613331     PISSN: None     EISSN: 21611653     Source Type: Journal    
DOI: 10.1021/acsmacrolett.7b00950     Document Type: Article

References (55)

1. Shoda, S.-i.; Uyama, H.; Kadokawa, J.-i.; Kimura, S.; Kobayashi, S. Enzymes as Green Catalysts for Precision Macromolecular Synthesis Chem. Rev. 2016, 116, 2307-2413 10.1021/acs.chemrev.5b00472
2. Tran, D. N.; Balkus, K. J. Perspective of Recent Progress in Immobilization of Enzymes ACS Catal. 2011, 1, 956-968 10.1021/cs200124a
3. Zhang, Y.; Ge, J.; Liu, Z. Enhanced Activity of Immobilized or Chemically Modified Enzymes ACS Catal. 2015, 5, 4503-4513 10.1021/acscatal.5b00996
4. DiCosimo, R.; McAuliffe, J.; Poulose, A. J.; Bohlmann, G. Industrial use of immobilized enzymes Chem. Soc. Rev. 2013, 42, 6437-6474 10.1039/c3cs35506c
5. Emery, O.; Lalot, T.; Brigodiot, M.; Maréchal, E. Free-radical polymerization of acrylamide by horseradish peroxidase-mediated initiation J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 3331-3333 10.1002/(SICI)1099-0518(19971115)35:15<3331::AID-POLA27>3.0.CO;2-B
6. Ikeda, R.; Tanaka, H.; Uyama, H.; Kobayashi, S. Laccase-catalyzed polymerization of acrylamide Macromol. Rapid Commun. 1998, 19, 423-425 10.1002/(SICI)1521-3927(19980801)19:8<423::AID-MARC423>3.0.CO;2-K
7. Kalra, B.; Gross, R. A. Horseradish Peroxidase Mediated Free Radical Polymerization of Methyl Methacrylate Biomacromolecules 2000, 1, 501-505 10.1021/bm005576v
8. Singh, A.; Ma, D.; Kaplan, D. L. Enzyme-Mediated Free Radical Polymerization of Styrene Biomacromolecules 2000, 1, 592-596 10.1021/bm005537j
9. Johnson, L. M.; Fairbanks, B. D.; Anseth, K. S.; Bowman, C. N. Enzyme-Mediated Redox Initiation for Hydrogel Generation and Cellular Encapsulation Biomacromolecules 2009, 10, 3114-3121 10.1021/bm900846m
10. Mao, Y.; Su, T.; Wu, Q.; Liao, C.; Wang, Q. Dual enzymatic formation of hybrid hydrogels with supramolecular-polymeric networks Chem. Commun. 2014, 50, 14429-14432 10.1039/C4CC06472K
11. Attieh, M. D.; Zhao, Y.; Elkak, A.; Falcimaigne-Cordin, A.; Haupt, K. Enzyme-Initiated Free-Radical Polymerization of Molecularly Imprinted Polymer Nanogels on a Solid Phase with an Immobilized Radical Source Angew. Chem., Int. Ed. 2017, 56, 3339-3343 10.1002/anie.201612667
12. Silva, T. B.; Spulber, M.; Kocik, M. K.; Seidi, F.; Charan, H.; Rother, M.; Sigg, S. J.; Renggli, K.; Kali, G.; Bruns, N. Hemoglobin and Red Blood Cells Catalyze Atom Transfer Radical Polymerization Biomacromolecules 2013, 14, 2703-2712 10.1021/bm400556x
13. Ng, Y.-H.; di Lena, F.; Chai, C. L. L. Metalloenzymatic radical polymerization using alkyl halides as initiators Polym. Chem. 2011, 2, 589-594 10.1039/C0PY00139B
14. Sigg, S. J.; Seidi, F.; Renggli, K.; Silva, T. B.; Kali, G.; Bruns, N. Horseradish Peroxidase as a Catalyst for Atom Transfer Radical Polymerization Macromol. Rapid Commun. 2011, 32, 1759-1759 10.1002/marc.201100579
15. Zhang, B.; Wang, X.; Zhu, A.; Ma, K.; Lv, Y.; Wang, X.; An, Z. Enzyme-Initiated Reversible Addition-Fragmentation Chain Transfer Polymerization Macromolecules 2015, 48, 7792-7802 10.1021/acs.macromol.5b01893
16. Danielson, A. P.; Van Kuren, D. B.; Lucius, M. E.; Makaroff, K.; Williams, C.; Page, R. C.; Berberich, J. A.; Konkolewicz, D. Well-Defined Macromolecules Using Horseradish Peroxidase as a RAFT Initiase Macromol. Rapid Commun. 2016, 37, 362-367 10.1002/marc.201500633
17. Fodor, C.; Gajewska, B.; Rifaie-Graham, O.; Apebende, E. A.; Pollard, J.; Bruns, N. Laccase-catalyzed controlled radical polymerization of N-vinylimidazole Polym. Chem. 2016, 7, 6617-6625 10.1039/C6PY01261B
18. Kurioka, H.; Komatsu, I.; Uyama, H.; Kobayashi, S. Enzymatic oxidative polymerization of alkylphenols Macromol. Rapid Commun. 1994, 15, 507-510 10.1002/marc.1994.030150609
19. Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Biochemical synthesis of water soluble polyanilines: Poly(p-aminobenzoic acid) Macromol. Rapid Commun. 1996, 17, 859-863 10.1002/marc.1996.030171203
20. Ma, K.; An, Z. Enzymatically Crosslinked Emulsion Gels Using Star-Polymer Stabilizers Macromol. Rapid Commun. 2016, 37, 1593-1597 10.1002/marc.201600283
21. Obinger, C.; Burner, U.; Ebermann, R. Generation of hydrogen peroxide by plant peroxidases mediated thiol oxidation Phyton 1997, 37, 219-226
22. Gantumur, E.; Sakai, S.; Nakahata, M.; Taya, M. Cytocompatible Enzymatic Hydrogelation Mediated by Glucose and Cysteine Residues ACS Macro Lett. 2017, 6, 485-488 10.1021/acsmacrolett.7b00122
23. Zavada, S. R.; McHardy, N. R.; Scott, T. F. Oxygen-mediated enzymatic polymerization of thiol-ene hydrogels J. Mater. Chem. B 2014, 2, 2598-2605 10.1039/C3TB21794A
24. Singh, S.; Topuz, F.; Hahn, K.; Albrecht, K.; Groll, J. Embedding of Active Proteins and Living Cells in Redox-Sensitive Hydrogels and Nanogels through Enzymatic Cross-Linking Angew. Chem., Int. Ed. 2013, 52, 3000-3003 10.1002/anie.201206266
25. Zhang, H.; Trout, W. S.; Liu, S.; Andrade, G. A.; Hudson, D. A.; Scinto, S. L.; Dicker, K. T.; Li, Y.; Lazouski, N.; Rosenthal, J.; Thorpe, C.; Jia, X.; Fox, J. M. Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation J. Am. Chem. Soc. 2016, 138, 5978-5983 10.1021/jacs.6b02168
26. Kade, M. J.; Burke, D. J.; Hawker, C. J. The Power of Thiol-ene Chemistry J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 743-750 10.1002/pola.23824
27. Dondoni, A. The Emergence of Thiol-Ene Coupling as a Click Process for Materials and Bioorganic Chemistry Angew. Chem., Int. Ed. 2008, 47, 8995-8997 10.1002/anie.200802516
28. Lowe, A. B. Thiol-ene ″click″ reactions and recent applications in polymer and materials synthesis: a first update Polym. Chem. 2014, 5, 4820-4870 10.1039/C4PY00339J
29. Tasdelen, M. A. Diels-Alder ″click″ reactions: recent applications in polymer and material science Polym. Chem. 2011, 2, 2133-2145 10.1039/c1py00041a
30. Gandini, A. The furan/maleimide Diels-Alder reaction: A versatile click-unclick tool in macromolecular synthesis Prog. Polym. Sci. 2013, 38, 1-29 10.1016/j.progpolymsci.2012.04.002
31. Becer, C. R.; Hoogenboom, R.; Schubert, U. S. Click Chemistry beyond Metal-Catalyzed Cycloaddition Angew. Chem., Int. Ed. 2009, 48, 4900-4908 10.1002/anie.200900755
32. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Applications of Orthogonal ″Click″ Chemistries in the Synthesis of Functional Soft Materials Chem. Rev. 2009, 109, 5620-5686 10.1021/cr900138t
33. Sumerlin, B. S.; Vogt, A. P. Macromolecular Engineering through Click Chemistry and Other Efficient Transformations Macromolecules 2010, 43, 1-13 10.1021/ma901447e
34. Espeel, P.; Du Prez, F. E. ″Click″-Inspired Chemistry in Macromolecular Science: Matching Recent Progress and User Expectations Macromolecules 2015, 48, 2-14 10.1021/ma501386v
35. Tasdelen, M. A.; Kiskan, B.; Yagci, Y. Externally stimulated click reactions for macromolecular syntheses Prog. Polym. Sci. 2016, 52, 19-78 10.1016/j.progpolymsci.2015.09.003
36. Blasco, E.; Sims, M. B.; Goldmann, A. S.; Sumerlin, B. S.; Barner-Kowollik, C. 50th Anniversary Perspective: Polymer Functionalization Macromolecules 2017, 50, 5215-5252 10.1021/acs.macromol.7b00465
37. Hansell, C. F.; Espeel, P.; Stamenovic, M. M.; Barker, I. A.; Dove, A. P.; Du Prez, F. E.; O'Reilly, R. K. Additive-Free Clicking for Polymer Functionalization and Coupling by Tetrazine-Norbornene Chemistry J. Am. Chem. Soc. 2011, 133, 13828-13831 10.1021/ja203957h
38. Zhang, L.-J.; Dong, B.-T.; Du, F.-S.; Li, Z.-C. Degradable Thermoresponsive Polyesters by Atom Transfer Radical Polyaddition and Click Chemistry Macromolecules 2012, 45, 8580-8587 10.1021/ma3016213
39. Conradi, M.; Junkers, T. Fast and Efficient 2 + 2 UV Cycloaddition for Polymer Modification via Flow Synthesis Macromolecules 2014, 47, 5578-5585 10.1021/ma500751j
40. Chen, J.; Yu, C.; Shi, Z.; Yu, S.; Lu, Z.; Jiang, W.; Zhang, M.; He, W.; Zhou, Y.; Yan, D. Ultrathin Alternating Copolymer Nanotubes with Readily Tunable Surface Functionalities Angew. Chem., Int. Ed. 2015, 54, 3621-3625 10.1002/anie.201408290
41. He, L.; Szopinski, D.; Wu, Y.; Luinstra, G. A.; Theato, P. Toward Self-Healing Hydrogels Using One-Pot Thiol-Ene Click and Borax-Diol Chemistry ACS Macro Lett. 2015, 4, 673-678 10.1021/acsmacrolett.5b00336
42. Xu, J.; Boyer, C. Visible Light Photocatalytic Thiol-Ene Reaction: An Elegant Approach for Fast Polymer Postfunctionalization and Step-Growth Polymerization Macromolecules 2015, 48, 520-529 10.1021/ma502460t
43. Zheng, J.; Hua, G.; Yu, J.; Lin, F.; Wade, M. B.; Reneker, D. H.; Becker, M. L. Post-Electrospinning "Triclick" Functionalization of Degradable Polymer Nanofibers ACS Macro Lett. 2015, 4, 207-213 10.1021/mz500759n
44. Gody, G.; Roberts, D. A.; Maschmeyer, T.; Perrier, S. A New Methodology for Assessing Macromolecular Click Reactions and Its Application to Amine-Tertiary Isocyanate Coupling for Polymer Ligation J. Am. Chem. Soc. 2016, 138, 4061-4068 10.1021/jacs.5b11831
45. Vandewalle, S.; Billiet, S.; Driessen, F.; Du Prez, F. E. Macromolecular Coupling in Seconds of Triazolinedione End-Functionalized Polymers Prepared by RAFT Polymerization ACS Macro Lett. 2016, 5, 766-771 10.1021/acsmacrolett.6b00342
46. Xiao, L.; Chen, Y.; Zhang, K. Efficient Metal-Free ″Grafting Onto″ Method for Bottlebrush Polymers by Combining RAFT and Triazolinedione-Diene Click Reaction Macromolecules 2016, 49, 4452-4461 10.1021/acs.macromol.6b00782
47. Zhang, J.; Zhang, M.; Du, F.-S.; Li, Z.-C. Synthesis of Functional Polycaprolactones via Passerini Multicomponent Polymerization of 6-Oxohexanoic Acid and Isocyanides Macromolecules 2016, 49, 2592-2600 10.1021/acs.macromol.6b00096
48. He, B.; Su, H.; Bai, T.; Wu, Y.; Li, S.; Gao, M.; Hu, R.; Zhao, Z.; Qin, A.; Ling, J.; Tang, B. Z. Spontaneous Amino-yne Click Polymerization: A Powerful Tool toward Regio- and Stereospecific Poly(beta-aminoacrylate)s J. Am. Chem. Soc. 2017, 139, 5437-5443 10.1021/jacs.7b00929
49. Macdougall, L. J.; Truong, V. X.; Dove, A. P. Efficient In Situ Nucleophilic Thiol-yne Click Chemistry for the Synthesis of Strong Hydrogel Materials with Tunable Properties ACS Macro Lett. 2017, 6, 93-97 10.1021/acsmacrolett.6b00857
50. Sun, H.; Kabb, C. P.; Dai, Y.; Hill, M. R.; Ghiviriga, I.; Bapat, A. P.; Sumerlin, B. S. Macromolecular metamorphosis via stimulus-induced transformations of polymer architecture Nat. Chem. 2017, 9, 817-823 10.1038/nchem.2730
51. Yuksekdag, Y. N.; Gevrek, T. N.; Sanyal, A. Diels-Alder ″Clickable″ Polymer Brushes: A Versatile Catalyst-Free Conjugation Platform ACS Macro Lett. 2017, 6, 415-420 10.1021/acsmacrolett.7b00041
52. Liu, Z.; Lv, Y.; An, Z. Enzymatic Cascade Catalysis for the Synthesis of Multiblock and Ultrahigh-Molecular-Weight Polymers with Oxygen Tolerance Angew. Chem., Int. Ed. 2017, 56, 13852-13856 10.1002/anie.201707993
53. Qiu, X.-P.; Winnik, F. M. Facile and efficient one-pot transformation of RAFT polymer end groups via a mild aminolysis/Michael addition sequence Macromol. Rapid Commun. 2006, 27, 1648-1653 10.1002/marc.200600436
54. Abel, B. A.; McCormick, C. L. ″One-Pot″ Aminolysis/Thiol Maleimide End-Group Functionalization of RAFT Polymers: Identifying and Preventing Michael Addition Side Reactions Macromolecules 2016, 49, 6193-6202 10.1021/acs.macromol.6b01512
55. Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6 th ed.; John Wiley & Sons, Inc.: New York, 1998.