Chemoselective polymerization of a phenol derivative having a methacryl group by peroxidase catalyst

Macromolecules

Volumn 31, Issue 2, 1998, Pages 554-556

  Uyama, Hiroshi ^a   Lohavisavapanich, Chakapan ^b   Ikeda, Ryohei ^b   Kobayashi, Shiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CROSSLINKING; DERIVATIVES; DIFFERENTIAL SCANNING CALORIMETRY; ENZYMES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; POLYMERIZATION; SOLUBILITY; THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS;

CHEMOSELECTIVE POLYMERIZATION; PEROXIDASE;

POLYACRYLATES;

EID: 0031646273     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma971510p     Document Type: Article

References (36)

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24. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
25. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
26. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
27. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
28. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
29. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
30. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
31. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
32. For recent papers on enzymatic oxidative polymerization of phenol derivatives, see: (a) Uyama, H.; Kurioka, H.; Kaneko, I.; Kobayashi, S. Chem. Lett. 1994, 423. (b) Wang, P.; Martin, B. D.; Parida, S.; Rethwisch, D. G.; Dordick, J. S. J. Am. Chem. Soc. 1995, 117, 12885. (c) Uyama, H.; Kurioka, H.; Sugihara, J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 189. (d) Ayyagari, M.; Akkara, J. A.; Kaplan, D. L. Acta Polym. 1996 47 193. (e) Premachandran, R. S.; Banerjee, S.; Wu, X.-K.; John, V. T.; McPherson, G. L.; Akkara, J. A.; Ayyagari, M.; Kaplan, D. L. Macromolecules 1996, 29, 6452. (f) Ikeda, R.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 3053. (g) Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Macromolecules 1996, 29, 8702. (h) Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1453. (i) Uyama, H.; Kurioka, H.; Kobayashi, S. Polym. J. 1997, 29, 190. (j) Alva, K. S.; Nayak, P. L.; Kumar, J.; Tripathy, S. K. J. Macromol. Sci. - Pure Appl. Chem. 1997, A34, 665. (k) Alva, K. S.; Marx, K. A.; Kumar, J.; Tripathy, S. K. Macromol. Rapid Commun. 1997, 18, 133.
33. Lowe, J.; Holdcroft, S. Macromolecules 1995, 28, 4608.
34. Derango, R. A.; Chiang, L.-C.; Dowbenko, R.; Lasch, J. G. Biotechnol. Techniques 1992, 6, 523.
35. 1 was synthesized by the regioselective acylation of 4-(2-hydoxyethyl)phenol with vinyl methacrylate using Pseudomonas cepacia lipase as catalyst: Ikeda, R. Japan Patent JP 95-58336, 1995.
36. The following is a procedure for the polymerization. 1 (0.41 g, 2.0 mmol) and HRP (4 mg) was dissolved in a mixture of acetone (5.0 mL) and phosphate buffer (5.0 mL). The polymerization was started by the addition of 30% hydrogen peroxide (23 μL, 0.20 mmol). The same amount of hydrogen peroxide was added every 15 min for 9 times. The reaction mixture was vigorously stirred under air at room temperature. After 24 h, the polymer was isolated by centrifugation. The residue was dried in vacuo to give 0.32 g of the polymer (yield 77%).