Biocatalytic synthesis of conducting polymers and prospects for its application

Biochemistry (Moscow)

Volumn 78, Issue 13, 2013, Pages 1539-1553

  Otrokhov, G V ^a   Morozova, O V ^a   Vasil'eva, I S ^a   Shumakovich, G P ^a   Zaitseva, E A ^b   Khlupova, M E ^a   Yaropolov, A I ^a  

^a BACH INSTITUTE OF BIOCHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Conducting polymer; Enzymatic polymerization; Laccase; Peroxi dase; Physicochemical properties; Practical application; Redox mediator

Indexed keywords

ENZYME; POLYMER;

BIOCATALYSIS; BIOTECHNOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; REVIEW; SYNTHESIS;

BIOCATALYSIS; BIOTECHNOLOGY; ENZYMES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYMERS;

EID: 84902519403     PISSN: 00062979     EISSN: 16083040     Source Type: Journal    
DOI: 10.1134/S0006297913130117     Document Type: Review

References (146)

1. Syed, A. A., and Dinesan, M. K. (1991) Talanta, 38, 815-837.
2. Diaz, A. F., Rubinson J. F., and Mark, H. B. (1988) Adv. Polym. Sci., 84, 113-139.
3. Rao, P. S., Sathyanarayana, D. N., and Jeevananda, T. (2001) Advanced Functional Molecules and Polymers, Gordon and Breach, Tokyo.
4. Chandrakanthi, N., and Careem, M. A. (2000) Polym. Bull., 45, 113-120.
5. Genies, E. M., Boyle, A., Lapkowski, M., and Tsintavis, C. (1990) Synth. Met., 36, 139-182.
6. Pron, A., and Rannou, P. (2002) Prog. Polym. Sci., 27, 135-190.
7. Machida, S., Miyata, S., and Techagumpuch, A. (1989) Synth. Met., 31, 311-318.
8. George, P. M., Lyckman, A. W., LaVan, D. A., Hegde, A., Leung, Y., Avasare, R., Testa, C., Alexander, P. M., Langer, R., and Sur, M. (2005) Biomaterials, 26, 3511-3519.
9. Bredas, J. L., Chance, R. R., and Silbey, R. (1982) Phys. Rev. B., 26, 5843-5854.
10. Bredas, J. L., Themans, B., Andre, J. M., Chance, R. R., and Silbey, R. (1984) Synth. Met., 9, 265-274.
11. Bredas, J. L., and Street, G. B. (1985) Acc. Chem. Res., 18, 309-315.
12. Bocchi, V., Chierici, L., Gardini, G. P., Mondelli, R., Bocchi, V., Chierici, L., Gardini, G. P., and Mondelli, R. (1970) Tetrahedron, 26, 4073-4082.
13. Joo, J., Lee, J. K., Baeck, J. S., Kim, K. H., Oh, E. J., and Epstein, J. (2001) Synth. Met., 117, 45-51.
14. Gursoy, S. S., Uygun, A., and Tilki, T. (2010) J. Macromol. Sci. Pure Appl. Chem., 47, 681-688.
15. Zheng, H., Shi, Q., Du, K., Mei, Y., and Zhang, P. (2013) Mol. Divers., doi: 10.1007/s11030-013-9426-1.
16. Lee, G. J., Lee, S. H., Ahn, K. S., and Kim, K. H. (2002) J. Appl. Polym. Sci., 84, 2583-2590.
17. Oh, E. J., and Jang, K. S. (2001) Synth. Met., 119, 109-110.
18. Qi, Z., and Pickup, P. G. (1997) Chem. Mater., 9, 2934-2939.
19. Armes, S. P. (1987) Synth. Met., 20, 365-371.
20. Machida, S., Miyata, S., and Techagumpuch, A. (1989) Synth. Met., 31, 311-318.
21. Rapi, S., Bocchi, V., and Gardini, G. P. (1988) Synth. Met., 24, 217-221.
22. Chao, T. H., and March, J. (1988) J. Polym. Sci., Part A: Polym. Chem., 26, 743-753.
23. Menshikova, A. Y., Shabsels, B. M., and Evseeva, T. G. (2003) Zh. Prikl. Khim., 76, 851-855.
24. Dhawan, S. K., and Trivedi, D. C. (1993) Bull. Mater. Sci., 16, 371-380.
25. Sun, B., Jones, J. J., Burford, R. P., and Skyllas-Kazacos, M. (1989) J. Mater. Sci., 24, 4024-4029.
26. Whang, Y. E., Han, J. H., Motobe, T., Watanabe, T., and Miyata, S. (1991) Synth. Met., 45, 151-161.
27. Scharifker, B. R., Garcia-Pastoriza, E., and Marino, W. (1991) J. Electroanal. Chem., 300, 85-98.
28. Yamaura, M., Sato, K., and Hagiwara, T. (1991) Synth. Met., 41, 439-442.
29. Bradner, F. P., and Shapiro, J. S. (1988) Synth. Met., 26, 69-77.
30. Imisides, M. D., John, R., Riley, P. J., and Wallace, G. G. (1991) Electroanalysis, 3, 879-884.
31. John, R., and Wallace, G. G. (1992) Polym. Int., 27, 255-260.
32. Roncali, J., Blanchard, Ph., and Frere, P. (2005) J. Mater. Chem., 15, 1589-1610.
33. Czardybon, A., and Lapkowski, M. (2001) Synth. Met., 119, 161-162.
34. Pyshkina, O., Kubarkov, A., and Sergeyev, V. (2010) Sci. J. Riga Tech. Univ., 21, 51-54.
35. Baika, W., Luana, W., Zhaoa, R. H., Kooa, S., and Kimb, K.-S. (2009) Synth. Met., 159, 1244-1246.
36. Kumar, A., and Reynolds, J. (1996) Macromolecules, 29, 7629-7630.
37. Aasmundtveit, K. E., Samuelsen, E. J., Pettersson, L. A. A., Inganas, O., Johansson, T., and Feidenhans'l, R. (1999) Synth. Met., 101, 561-564.
38. Wu, C.-H., Don, T.-M., and Chiu, W.-Y. (2011) Polymer, 52, 1375-1384.
39. Gok, A., Omastova, M., and Yavuz, A. G. (2007) Synth. Met., 157, 23-29.
40. Groenendaal, L. B., Jonas, F., Freitag, D., Pielartzik, H., and Reynolds, J. R. (2000) Adv. Mater., 12, 481-494.
41. Groenendaal, L. B., Zotti, G., Aubert, P., Waybright, S. M., and Reynolds, J. R. (2003) Adv. Mater., 15, 855-879.
42. Randrimahazaka, H., Noel, C., and Chevrot, C. (1999) J. Electroanal. Chem., 472, 103-111.
43. Yamato, H., Ohwa, M., and Wernet, W. (1995) J. Electroanal. Chem., 397, 163-170.
44. Yamato, H., Kai, K., Ohwa, M., Asakura, T., Koshiba, T., and Wernet, W. (1996) Synth. Met., 83, 125-130.
45. Yamato, H., Kai, K.-I., Ohwa, M., Wernet, W., and Matsumura, M. (1997) Electrochim. Acta, 42, 2517-2523.
46. Lima, A., Schottland, P., Sadki, S., and Chevrot, C. (1998) Synth. Met., 93, 33-41.
47. Sakmeche, N., Aaron, J. J., Fall, M., Aeiyach, S., Jouini, M., Lacroix, J. C., and Lacaze, P. C. (1996) Chem. Commun., 24, 2723-2724.
48. Lee, Y., Park, S., and Son, Y. (1999) Mol. Cryst. Liq. Cryst., 327, 237-240.
49. Kudoh, Y., Akami, K., and Matsuya, Y. (1998) Synth. Met., 98, 65-70.
50. Witayakran, S., and Ragauskas, A. J. (2009) Adv. Synth. Catal., 351, 1187-1209.
51. Kunamneni, A., Camarero, S., Garcia-Burgos, C., Plou, F. J., Ballesteros, A., and Alcalde, M. (2008) Microb. Cell Factories, 7, 32; doi: 10.1186/1475-2859-7-32.
52. Santaniello, E., Ferraboschi, P., Grisenti, P., and Manzocchi, A. (1992) Chem. Rev., 92, 1071-1140.
53. Seoane, G. (2000) Curr. Org. Chem., 4, 283-304.
54. Farrell, R. L., Murtagh, K. E., Tien, M., Mozuch, M. D., and Kirk, T. K. (1989) Enzyme Microb. Technol., 11, 322-328.
55. Wakamatsu, K., and Takahama, U. (1993) Physiol. Plants, 88, 167-171.
56. Dunford, H. B. (1991) Peroxidases in Chemistry and Biology, Vol. 2, CRC Press, Inc., pp. 1-24.
57. McEldoon, J. P., and Dordick, J. S. (1996) Biotechnol. Prog., 12, 555-558.
58. Nissum, M., Schodt, C. B., and Welinder, K. G. (2001) Biochim. Biophys. Acta, 1545, 339-348.
59. Sakharov, I. Y. (2004) Biochemistry (Moscow), 69, 823-829.
60. Gazaryan, I. G., and Lagrimini, L. M. (1996) Phytochemistry, 41, 1029-1034.
61. Kokkinakis, D. M., and Brooks, J. L. (1979) Plant Physiol., 63, 93-99.
62. Chance, B. (1949) Science, 109, 204-208.
63. Jones, P., and Dunford, H. B. (1977) Dokl. Bolg. Akad. Nauk, 5, 121-134.
64. Yoshida, H. (1883) J. Chem. Soc. Trans., 43, 472-486.
65. Baldrian, P. (2006) FEMS Microbiol. Rev., 30, 215-242.
66. Thurston, C. F. (1994) Microbiology, 140, 19-26.
67. Claus, H. (2004) Micron, 35, 93-96.
68. Morozova, O. V., Shumakovich, G. P., Gorbacheva, M. A., Shleev, S. V., and Yaropolov, A. I. (2007) Biochemistry (Moscow), 72, 1136-1150.
69. Lee, S.-K., George, S. D., Antholine, W. E., Hedman, B., Hodgson, K. O., and Solomon, E. I. (2002) J. Am. Chem. Soc., 124, 6180-6193.
70. Mayer, A. M., and Staples, R. C. (2002) Phytochemistry, 60, 551-565.
71. Riva, S. (2006) Trends Biotechnol., 24, 219-226.
72. Yaropolov, A. I., Skorobogat'ko, O. V., Vartanov, S. S., and Varfolomeyev, S. D. (1994) Appl. Biochem. Biotechnol., 49, 257-280.
73. Baldrian, P. (2004) Appl. Microbiol. Biotechnol., 63, 560-563.
74. Kurniawati, S., and Nicell, J. A. (2008) Bioresour. Technol., 99, 7825-7834.
75. Shin, K. S., and Lee, Y. J. (2000) Arch. Biochem. Biophys., 384, 109-115.
76. Shleev, S. V., Morozova, O. V., Nikitina, O. V., Gorshina, E. S., Rusinova, T. V., Serezhenkov, V. A., Burbaev, D. S., Gazaryan, I. G., and Yaropolov, A. I. (2004) Biochimie, 86, 693-703.
77. Shiba, T., Xiao, L., Miyakoshi, T., and Chen, C.-L. (2000) J. Mol. Catal. B: Enzym., 10, 605-615.
78. Bertrand, T., Jolivalt, C., Caminade, E., Joly, N., Mougin, C., and Briozzo, P. (2002) Acta Cryst., D58, 319-321.
79. Polyakov, K. M., Fedorova, T. V., Stepanova, E. V., Cherkashin, E. A., Kurzeev, S. A., Strokopytov, B. V., Lamzin, V. S., and Koroleva, O. V. (2009) Acta Cryst., D65, 611-617.
80. Morozova, O. V., Shumakovich, G. P., Shleev, S. V., and Yaropolov, A. I. (2007) Prikl. Biochim. Mikrobiol., 43, 583-597.
81. Solomon, E. I., Sundaram, U. M., and Machonkin, T. E. (1996) Chem. Rev., 96, 2563-2606.
82. Bento, I., Martins, L. O., Gato, L. G., Armenia, C. M., and Lindley, P. F. (2005) Dalton Transact., 21, 3507-3513.
83. Solomon, E. I., Chen, P., Metz, M., Lee, S. K., and Palmer, A. E. (2001) Angew. Chem. Int. Ed. Engl., 40, 4570-4590.
84. Bourbonnais, R., and Paice, M. G. (1990) FEBS, 267, 99-102.
85. Fabbrini, M., Galli, C., and Gentili, P. (2002) J. Mol. Catal. B: Enzym., 16, 231-240.
86. Shimizu, A., Kwon, J.-H., Sasaki, T., Satoh, T., Sakurai, N., Sakurai, T., Yamaguchi, S., and Samejima, T. (1999) Biochemistry, 38, 3034-3042.
87. Bankar, S. B., Bule, M. V., Singhal, R. S., and Ananthanarayan, L. (2009) Biotech. Adv., 27, 489-501.
88. Sztajer, H., Wang, W., Lunsdorf, H., Stocker, A., and Schmid, R. D. (1996) Appl. Microbiol. Biotechnol., 45, 600-606.
89. Kobayashi, S., and Makino, A. (2009) Chem. Rev., 109, 5288-5353.
90. Bouldin, R., Kokil, A., Ravichandran, S., Nagarajan, S., Kumar, J., Samuelson, L. A., Bruno, F. F., and Nagarajan, R. (2010) Green Polymer Chem. Biocatal. Biomater. ACS Symp. Ser., 1043, 315-341.
91. Walde, P., and Guo, Z. (2011) Soft Matter, 7, 316-331.
92. Xu, P., Singh, A., and Kaplan, D. (2006) Adv. Polym. Sci., 194, 69-94.
93. Hollmann, F., and Arends, I. W. C. E. (2012) Polymers, 4, 759-793.
94. McEldoon, J. P., and Dordick, J. S. (1996) Biotechnol. Prog., 12, 555-558.
95. Sakharov, I. Y., and Sakharova, I. V. (2002) Biochim. Biophys. Acta, 1598, 108-114.
96. Vasil'eva, I. S., Morozova, O. V., Shumakovich, G. P., Shleev, S. V., Sakharov, I. Y., and Yaropolov, A. I. (2007) Synth. Met., 157, 684-689.
97. USA Patent No. 5,420,237 (1995).
98. Cruz-Silva, R., Romero-Garcia, J., Angulo-Sanchez, J. L., Ledezma-Perez, A., Arias-Marin, E., Moggio, I., and Flores-Loyola, E. (2005) Eur. Polym. J., 41, 1129-1135.
99. Kausaite, A., Ramanaviciene, A., and Ramanavicius, A. (2009) Polymer, 50, 1846-1851.
100. Cui, X., Li, C. M., Zang, J., Zhou, Q., Gan, Y., Bao, H., Guo, J., Lee, V. S., and Moochhala, S. M. (2007) J. Phys. Chem. C, 111, 2025-2031.
101. Aizawa, M., Wang, L., Shinohara, H., and Ikariyama, Y. (1990) J. Biotechnol., 14, 301-309.
102. Samuelson, L. A., Anagnostopoulos, A., Alva, K. S., Kumar, J., and Tripathy, S. K. (1998) Macromolecules, 31, 4376-4378.
103. Liu, W., Kumar, J., Tripathy, S., Senecal, K. J., and Samuelson, L. (1999) J. Am. Chem. Soc., 121, 71-78.
104. Karamyshev, A. V., Shleev, S. V., Koroleva, O. V., Yaropolov, A. I., and Sakharov, I. Y. (2003) Enzyme Microb. Technol., 33, 556-564.
105. Mazhuto, Y. M., Karamyshev, A. V., Shleev, S. V., Sakharov, I. Y., and Yaropolov, A. I. (2005) Prikl. Biokhim. Mikrobiol., 41, 247-250.
106. Shumakovich, G. P., Vasil'eva, I. S., Morozova, O. V., Khomenkov, V. G., Staroverova, I. N., Budashov, I. A., Kurochkin, I. N., Boyeva, J. A., Sergeyev, V. G., and Yaropolov, A. I. (2010) J. Appl. Polym. Sci., 117, 1544-1550.
107. Shen, Y., Sun, J., Wu, J., and Zhon, Q. (2005) J. Appl. Polym. Sci., 96, 814-817.
108. Nagarajan, R., Liu, W., Kumar, J., Tripathy, S. K., Bruno, F. F., and Samuelson, L. A. (2001) Macromolecules, 34, 3921-3927.
109. Nickels, P., Dittmer, W. U., Beyer, S., Kotthaus, J. P., and Simmel, F. C. (2004) Nanotechnology, 15, 1521-1529.
110. Cruz-Silva, R., Amaro, E., Escamilla, A., Nicho, M. E., Sepulveda-Guzman, S., Arizmendi, L., Romero-Garcia, J., Castillon-Barraza, F. F., and Farias, M. H. (2008) J. Colloid Interface Sci., 328, 263-269.
111. Sahoo, S. K., Nagarajan, R., Roy, S., Samuelson, L. A., Kumar, J., and Cholli, A. L. (2004) Macromolecules, 37, 4130-4138.
112. Samuelson, L., Liu, W., Nagarajan, R., Kumar, J., Bruno, F. F., Cholli, A., and Tripathy, S. (2001) Synth. Met., 119, 271-272.
113. Streltsov, A. V., Shumakovich, G. P., Morozova, O. V., Gorbacheva, M. A., and Yaropolov, A. I. (2008) Appl. Biochem. Microb., 44, 264-270.
114. Rumbau, V., Pomposo, J. A., Alduncin, J. A., Grande, H., Mecerreyes, D., and Ochoteco, E. (2007) Enzyme Microb. Technol., 40, 1412-1421.
115. Guo, Z., Ruuegger, H., Kissner, R., Ishikawa, T., Willeke, M., and Walde, P. (2009) Langmuir, 25, 11390-11405.
116. Liu, W., Cholli, A. L., Nagarajan, R., Kumar, J., Tripathy, S., Bruno, F. F., and Samuelson, L. (1999) J. Am. Chem. Soc., 121, 11345-11355.
117. Cruz-Silva, R., Ruiz-Flores, C., Arizmendi, L., Romero-Garcia, J., Arias-Marin, E., Moggio, I., Castillon, F. F., and Farias, M. H. (2006) Polymer, 47, 1563-1568.
118. Caramyshev, A. V., Evtushenko, E. G., Ivanov, V. F., Barcelo, A. R., Roig, M. G., Shnyrov, V. L., van Huystee, R. B., Kurochkin, I. N., Vorobiev, A. K., and Sakharov, I. Y. (2005) Biomacromolecules, 6, 1360-1366.
119. Longoria, A. M., Hu, H., and Vazquez-Duhalt, R. (2010) Appl. Biochem. Biotech., 162, 927-934.
120. Roman, P., Cruz-Silva, R., and Vazquez-Duhalt, R. (2012) Synth. Met., 162, 794-799.
121. Streltsov, A. V., Morozova, O. V., Arkharova, N. A., Klechkovskaya, V. V., Staroverova, I. N., Shumakovich, G. P., and Yaropolov, A. I. (2009) J. Appl. Pol. Sci., 114, 928-934.
122. Jin, Z., Su, Y., and Duan, Y. (2001) Synth. Met., 122, 237-242.
123. Vasil'eva, I. S., Morozova, O. V., Shumakovich, G. P., and Yaropolov, A. I. (2009) Prikl. Biokhim. Mikrobiol., 45, 27-30.
124. Rumbau, V., Marcilla, R., Ochoteco, E., Pomposo, J. A., and Mecerreyes, D. (2006) Macromolecules, 39, 8547-8549.
125. Guo, H., Knobler, C. M., and Kaner, R. B. (1999) Synth. Met., 101, 44-47.
126. Moutet, J.-C., Saint-Aman, E., Tran-Van, F., Angibeaud, P., and Utille, J.-P. (1992) Adv. Mater., 4, 511-513.
127. Thiyagarajan, M., Samuelson, L. A., Kumar, J., and Cholli, A. L. (2003) J. Am. Chem. Soc., 125, 11502-11503.
128. Ashraf, S. A., Kane-Maguire, L. A. P., Majidi, M. R., Pyne, S. G., and Wallace, G. G. (1997) Polymer, 38, 2627-2631.
129. Kane-Maguire, L. A. P., MacDiarmid, A. G., Norris, I. D., Wallace, G. G., and Zheng, W. (1999) Synth. Met., 106, 171-176.
130. Zeifman, Y. S., Maiboroda, I. O., Grishchenko, Y. V., Morozova, O. V., Vasil'eva, I. S., Shumakovich, G. P., and Yaropolov, A. I. (2012) Prikl. Biokhim. Mikrobiol., 48, 169-174.
131. Tzou, K., and Gregory, R. V. (1992) Synth. Met., 47, 267-277.
132. Shumakovich, G., Streltsov, A., Gorshina, E., Rusinova, T., Kurova, V., Vasil'eva, I., Otrokhov, G., Morozova, O., and Yaropolov, A. (2011) J. Mol. Catal. B: Enzym., 69, 83-88.
133. Rumbau, V., Pomposo, J. A., Eleta, A., Rodriguez, J., Grande, H., Mecerreyes, D., and Ochoteco, E. (2007) Biomacromolecules, 8, 315-317.
134. Hawkins, S. L., and Ratcliffe, N. M. (2000) J. Mat. Chem., 10, 2057-2062.
135. Nagarajan, S., Kumar, J., Bruno, F. F., Samuelson, L. A., and Nagarajan, R. (2008) Macromolecules, 41, 3049-3052.
136. Shumakovich, G., Otrokhov, G., Vasil'eva, I., Pankratov, D., Morozova, O., and Yaropolov, A. (2012) J. Mol. Catal. B: Enzym., 81, 66-68.
137. Song, H.-K., Tayhas, G., and Palmore, R. (2005) J. Phys. Chem. B, 109, 19278-19287.
138. Kupriyanovich, Y. N., Sukhov, B. G., Medvedeva, S. A., Mikhaleva, A. I., Vakul'skaya, T. I., Myachina, G. F., and Trofimov, B. A. (2008) Mendel. Commun., 18, 56-58.
139. Shumakovich, G., Kurova, V., Vasil'eva, I., Pankratov, D., Otrokhov, G., Morozova, O., and Yaropolov, A. (2012) J. Mol. Catal. B: Enzym., 77, 105-110.
140. Riul, A., Jr., Malmegrim, R., Fonseca, F. J., and Mattoso, L. H. C. (2003) Biosens. Bioelect., 18, 1365-1369.
141. Wessling, B., and Posdorfer, J. (1999) Synth. Met., 102, 1400-1401.
142. Soto-Oviedo, M. A., Araujo, O. A., Faez, R., Rezende, M. C., and De Paoli, M.-A. (2006) Synth. Met., 156, 1249-1255.
143. Carpi, F., and De Rossi, D. (2006) Opt. Laser Technol., 38, 292-305.
144. Russian Federation Patent No. 2348455 of 10.10.2006.
145. Sheng, Q., and Zheng, J. (2009) Biosens. Bioelect., 24, 1621-1628.
146. Heider, G. H., Sasso, S. V., Huang, K., Yacynych, A. M., and Wieck, H. J. (1990) Anal. Chem., 62, 1106-1110.