In Vitro Enzyme-Induced Vinyl Polymerization

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Enzyme-Catalyzed Synthesis of Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 194))

Abstract

The in vitro enzyme-mediated polymerization of vinyl monomers is reviewed with a scope covering enzymatic polymerization of vitamin C functionalized vinyl monomers, styrene, derivatives of styrene, acrylates, and acrylamide in water and water-miscible cosolvents. Vitamin C functionalized polymers were synthesized via a two-step biocatalytic approach where vitamin C was first regioselectively coupled to vinyl monomers and then subsequently polymerized. The analysis of this enzymatic cascade approach to functionalized vinyl polymers showed that the vitamin C in polymeric form retained its antioxidant property. Kinetic and mechanistic studies revealed that a ternary system (horseradish peroxidase, H2O2, initiator β-diketone) was required for efficient polymerization and that the initiator controls the characteristics of the polymer. The main attributes of enzymatic approaches to vinyl polymerization when compared with more traditional synthetic approaches include facile ambient reaction environments of temperature and pressure, aqueous conditions, and direct control of selectivity to generate functionalized materials as described for the ascorbic acid modified polymers.

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References

  1. Kaplan DL, Dordick J, Gross RA, Swift G (1998) ACS Symp Ser 684:2

    CAS  Google Scholar 

  2. Singh A, Kaplan DL (2002) J Polym Environ 10:85

    Article  CAS  Google Scholar 

  3. Kobayashi S, Uyama H, Kimura S (2001) Chem Rev 101:3793

    Article  CAS  Google Scholar 

  4. Gross RA, Kumar A, Kalra B (2001) Chem Rev 101:2097

    Article  CAS  Google Scholar 

  5. Kobayashi S, Uyama H (2001) Adv Biochem Eng Biotechnol 71:241

    CAS  Google Scholar 

  6. Dordick JS, Marletta MA, Klibanov AM (1987) Biotechnol Bioeng 30:31

    Article  CAS  Google Scholar 

  7. Akkara JA, Senecal KJ, Kaplan DL (1991) J Polym Sci A-1 29:1561

    Article  CAS  Google Scholar 

  8. Rao AM, John VT, Gonzalez RD, Akkara JA, Kaplan DL (1993) Biotechnol Bioeng 41:531

    Article  CAS  Google Scholar 

  9. Karayigitoglu CF, Kommareddi N, Gozalez RD, John VT, McPherson GL, Akkara JA, Kaplan DL (1995) Mater Sci Eng C2:165

    CAS  Google Scholar 

  10. Akkara JA, Ayyagari M, Bruno F, Samuelson L, John VT, Karayigitoglu C, Tripathy S, Marx KA, Rao DVGLN, Kaplan DL (1994) Biomimetics 2:331

    CAS  Google Scholar 

  11. Ayyagari MS, Marx KA, Tripathy SK, Akkara JA, Kaplan DL (1995) Macromolecules 28:5192

    Article  CAS  Google Scholar 

  12. Ayyagari M, Akkara JA, Kaplan DL (1996) Mater Sci Eng C4:169

    CAS  Google Scholar 

  13. Akkara JA, Kaplan DL, John VT, Tripathy SK (1996) Polym Mater Encyc 3:2115

    Google Scholar 

  14. Banerjee S, John VT, McPherson GL, O'Conor CJ, Buisson YSL, Akkara JA, Kaplan DL (1997) Colloid Polym Sci 275:930

    Article  CAS  Google Scholar 

  15. Parravano G (1951) J Am Chem Soc 73:183

    CAS  Google Scholar 

  16. Derango RA, Chiang L, Dowbenko R, Lasch JG (1992) Biotechnol Lett 6:523

    CAS  Google Scholar 

  17. Xue C, Chen X (1997) Sichuan Lianhe Daxue Xuebao, Gongcheng Kexueban 1:41

    CAS  Google Scholar 

  18. Totsuka F, Sakakibara N, Osawa T (1997) JP 09157531 A2

    Google Scholar 

  19. Zhao X, Zheng Y, She Y, Zhang Y (1995) Jianghan Shiyou Xueyuan Xuebao 17:68

    CAS  Google Scholar 

  20. Suzuki T (1985) JP 60149609 A2

    Google Scholar 

  21. Mai C, Milstein O, Huttermann A (1999) Appl Microbiol Biotechnol 51:517

    Article  Google Scholar 

  22. Mai C, Milstein O, Huttermann A (2000) J Biotechnol 79:173

    Article  CAS  Google Scholar 

  23. Huttermann A, Kharazipour A (1996) VTT Symp 163:143

    Google Scholar 

  24. Ikeda R, Tanaka H, Uyama H, Kobayashi S (1998) Macromol Rapid Commun 19:423

    CAS  Google Scholar 

  25. Emery O, Lalot T, Brigodiot M, Marechal E (1997) J Polym Sci A-1 35:3331

    Article  CAS  Google Scholar 

  26. Teixeira D, Lalot T, Brigodiot M, Marechal E (1999) Macromolecules 32:70

    Article  CAS  Google Scholar 

  27. Kalra B, Gross RA (2002) Green Chem 4:174

    Article  CAS  Google Scholar 

  28. Uyama H, Lohavisavapanich C, Ikeda R, Kobayashi S (1998) Macromolecules 31:554

    Article  CAS  Google Scholar 

  29. Kalra B, Gross R (2000) Biomacromolecules 1:501

    Article  CAS  Google Scholar 

  30. Miller RL, Nielson LE (1961) J Polym Sci 55:643

    Article  CAS  Google Scholar 

  31. Eichhorn J (1964) J Appl Polym Sci 8:2497

    Article  CAS  Google Scholar 

  32. Singh A, Ma D, Kaplan DL (2000) Biomacromolecules 1:592

    Article  CAS  Google Scholar 

  33. Singh A, Roy S, Samuelson L, Bruno F, Nagarajan R, Kumar J, John V, Kaplan DL (2001) J Macromol Sci Pure Appl Chem A38:1219

    CAS  Google Scholar 

  34. Wei Z, Wang W, ** D, Yang D, Tartakovskaya L (1997) J Appl Polym Sci 64:1893

    Article  CAS  Google Scholar 

  35. Carretta N, Tricoli V, Picchioni F (2000) J Memb Sci 166:189

    Article  CAS  Google Scholar 

  36. Lam-Leung SY, Li HR (1995) J Appl Polym Sci 57:1373

    Article  CAS  Google Scholar 

  37. Goldammer EV, Conway BE (1973) J Polym Sci B 11:2767

    Google Scholar 

  38. Gryte CC, Gregor HP (1976) J Polym Sci B 14:1839

    CAS  Google Scholar 

  39. Kowalczynska HM, Nowak-Wyrzkowska M (1999) Cell Biol Int 23:359

    CAS  Google Scholar 

  40. Lee JH, Lee JW, Khang G, Lee HB (1997) Biomaterials 18:351

    Article  CAS  Google Scholar 

  41. Detrait E, Lhoest JB, Bertrand P, Van den Bosch de Aguilar P (1999) J Biomed Mater Res 45:404

    Article  CAS  Google Scholar 

  42. Charef S, Tapon-Bretaudiere J, Fischer A, Flunger F, Jozefowicz M, Labarre D (1996) Biomaterials 17:903

    Article  CAS  Google Scholar 

  43. Liekens S, Leali D, Neyts J, Esnouf R, Rusnati M, Dellera P, Maudgal PC, De Clercq E, Presta M (1999) Mol Pharmacol 56:204

    CAS  Google Scholar 

  44. Liekens S, Neyts J, Degreve B, De Clercq E (1997) Oncol Res 9:173

    CAS  Google Scholar 

  45. Zeitlin L, Whaley KJ, Hegarty TA, Moench TR, Cone RA (1997) Contraception 56:329

    Article  CAS  Google Scholar 

  46. Mohan P, Schols D, Baba M, De Clercq E (1992) Antiviral Res 18:139

    Article  CAS  Google Scholar 

  47. Tan GT, Wickramasinghe A, Verma S, Hughes SH, Pezzuto JM, Baba M, Mohan P (1993) Biochim Biophys Acta 1181:183

    CAS  Google Scholar 

  48. Ikeda S, Neyts J, Verma S, Wickramasinghe A, Mohan P, De Clercq E (1994) Antimicrobial Agents Chemother 38:256

    CAS  Google Scholar 

  49. Anderson RA, Feathergill K, Diao X, Cooper M, Kirkpatrick R, Spear P, Waller DP, Chany C, Doncel GF, Herold B, Zaneveld LJD (2000) J Androl 21:862

    CAS  Google Scholar 

  50. Herold BC, Bourne N, Marcellino D, Kirkpatrick R, Strauss DM, Zaneveld LJD, Waller DP, Anderson RA, Chany CJ, Barham BJ, Stanberry LR, Cooper MD (2000) J Infect Dis 181:770

    Article  CAS  Google Scholar 

  51. Luscher-Mattli M (2000) Antivir Chem Chemother 11:249

    CAS  Google Scholar 

  52. Breese KD, Lamethe JF, DeArmitt C (2000) Polym Degrad Stab 70:89 and references cited therein

    CAS  Google Scholar 

  53. Code of Federal Regulations, 21CFR172.110, Title 21, vol 3, parts 170–199, pp 28–29

    Google Scholar 

  54. Shephard AB, Nichols SC, Braithwaite A (1999) Talanta 48:585

    CAS  Google Scholar 

  55. Shephard AB, Nichols SC, Braithwaite A (1999) Talanta 48:595

    CAS  Google Scholar 

  56. Shephard AB, Nichols SC, Braithwaite A (1999) Talanta 48:607

    CAS  Google Scholar 

  57. Nickels H, Hackenberger A (1984) Ger Offen DE 3308922

    Google Scholar 

  58. Pauling H, Wehrli C (1998) Eur Pat Appl EP 296483

    Google Scholar 

  59. Watanabe Y, Adachi S, Nakanishi K, Matsuno R (2001) JAOCS 78:823

    CAS  Google Scholar 

  60. Luhong T, Hao Z, Shehate MM, Yunfei HA (2000) Biotechnol Appl Biochem 32:35

    Article  CAS  Google Scholar 

  61. Singh A, Kaplan DL (2003) Adv Mater 15:1291

    Article  CAS  Google Scholar 

  62. Singh A, Kaplan DL (2004) J Macromol Sci Pure Appl Chem 41:1377–1386

    Google Scholar 

  63. Chen Y, Wang M, Rosen RT, Ho C (1999) J Agric Food Chem 47:2226

    CAS  Google Scholar 

  64. Masuda T, Yonemori S, Oyama Y, Takeda Y, Tanaka T, Andoh T, Shinohara A, Nakata M (1999) J Agric Food Chem 47:1749

    CAS  Google Scholar 

  65. Duh P, Yen G, Yen W, Chang L (2001) J Agric Food Chem 49:1455

    Article  CAS  Google Scholar 

  66. Durand A, Lalot T, Brigodiot M, Marechal E (2000) Polymer 41:8183

    CAS  Google Scholar 

  67. Durand A, Lalot T, Brigodiot M, Marechal E (2001) Polymer 42:5515

    Article  CAS  Google Scholar 

  68. Lalot T, Brigodiot M, Marechal E (1999) Polym Int 48:288

    CAS  Google Scholar 

  69. Ashley PL, Griffin BW (1981) Arch Biochem Biophys 210:167

    Article  CAS  Google Scholar 

Download references

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Correspondence to David L. Kaplan .

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Shiro Kobayashi Helmut Ritter David Kaplan

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Singh, A., Kaplan, D.L. In Vitro Enzyme-Induced Vinyl Polymerization. In: Kobayashi, S., Ritter, H., Kaplan, D. (eds) Enzyme-Catalyzed Synthesis of Polymers. Advances in Polymer Science, vol 194. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_033

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