90
D. Popescu et al. / Journal of Molecular Catalysis B: Enzymatic 62 (2010) 81–90
methyl-2-butanol, a tertiary alcohol, which is non-reactive in
the lipase-catalyzed reaction but is a common solvent for both
reagents: diols/triols and (meth)acrylates. In addition this work
presents a detailed investigation of the enantio- and regioselectiv-
ity in the diols and triols as well as a detailed and elaborate analysis
of the product distributions.
The transacylation of MA and MMA with diols and triols is car-
ried out under mild conditions, is easy and rapid in processing,
being suitable for the preparation of sensitive monomers, as can
be depicted from this paper. The resulting monomers are ready for
polymerization without further purification, as will be shown in an
upcoming publication.
[13] M. Woundenberg-Van Oosterom, F. Van Rantwijk, R.A. Sheldon, Biotechnol.
Bioeng. 49 (1996) 328–333.
[14] Q. Jing, R.J. Kaziauskas, Chirality 20 (2008) 724–735.
[15] P. Gadler, K. Faber, Trends Biotechnol. 25 (2007) 83–88.
[16] W. Du, Y.Y. Xu, D.H. Liu, Z.B. Li, J. Mol. Catal. B-Enzym. 37 (2005) 68–71.
[17] M. Iso, B.X. Chen, M. Eguchi, T. Kudo, S. Shrestha, J. Mol. Catal. B-Enzym. 16
(2001) 53–58.
[18] J.S. Yang, G.J. Jeon, B.K. Hur, J.W. Yang, J. Microbiol. Biotechnol. 15 (2005)
1183–1188.
[19] S. Bloomer, P. Adlercreutz, B. Mattiasson, Enzyme Microb. Technol. 14 (1992)
546–552.
[20] Z.Y. Li, O.P. Ward, J. Am. Oil Chem. Soc. 70 (1993) 745–748.
[21] D. Popescu, H. Keul, M. Moeller, Macromol. Chem. Phys. 210 (2009) 123–139.
[22] M.Y. Sen, J.E. Puskas, S. Ummadisetty, J.P. Kennedy, Macromol. Rapid Commun.
29 (2008) 1598–1602.
[23] S. Ramaswamy, B. Morgan, A.C. Oehlschlager, Tetrahedron Lett. 31 (1990)
3405–3408.
[24] X.F. Li, M.H. Zong, R.D. Yang, J. Mol. Catal. B-Enzym. 38 (2006) 48–53.
[25] A.W.-Y. Chan, B. Ganem, Biocatal. Biotransform. 8 (1993) 163–169.
[26] A.B. Hajjar, P.F. Nicks, C. Knowles, J. Biotechnol. Lett. 12 (1990) 825–830.
[27] I. Ikeda, J. Tanaka, K. Suzuki, Tetrahedron Lett. 32 (1991) 6865–6866.
[28] R. Derango, Y.F. Wang, R. Dowbenko, L.C. Chiang, Biotechnol. Lett. 16 (1994)
241–246.
[29] S. Warwel, G. Steinke, A. Rusch, M.R. Klaas, Biotechnol. Technol. 10 (1996)
283–286.
[30] V. Athawale, N. Manjrekar, M. Athawale, Tetrahedron Lett. 43 (2002)
4797–4800.
[31] G. Burghard, H. Geoffrey (invs.), Goldschmidt GmbH, EP 0965645B1, 1999.
[32] S. Kobayashi, H. Uyama, S. Kimura, Chem. Rev. 101 (2001) 3793–3818.
[33] R.A. Gross, A. Kumar, B. Kalra, Chem. Rev. 101 (2001) 2097–2124.
[34] F. Binns, P. Harffey, S.M. Roberts, A. Taylor, J. Chem. Soc.-Perkin Trans. 1 (1999)
2671–2676.
[35] E.M. Anderson, M. Karin, O. Kirk, Biocatal. Biotransform. 16 (1998) 181–204.
[36] M. Hans, H. Keul, A. Heise, M. Moeller, Macromolecules 40 (2007) 8872–8880.
[37] M. Ferrer, J. Soliveri, F.J. Plou, N. Lopez-Cortes, D. Reyes-Duarte, M. Christensen,
J.L. Copa-Patino, A. Ballesteros, Enzyme Microb. Technol. 36 (2005) 391–398.
[38] F. Chamouleau, D. Coulon, M. Girardin, M. Ghoul, J. Mol. Catal. B-Enzym. 11
(2001) 949–954.
[39] Y. Watanabe, Y. Shimada, A. Sugihara, H. Noda, H. Fukuda, Y. Tominaga, J. Am.
Oil Chem. Soc. 77 (2000) 355–360.
[40] M.M. Soumanou, U.T. Bornscheuer, Enzyme Microb. Technol. 33 (2003) 97–103.
[41] Y. Watanabe, Y. Shimada, A. Sugihara, Y. Tominaga, J. Am. Oil Chem. Soc. 78
(2001) 703–707.
Acknowledgments
This work was carried out in the framework of the IP-project
“Sustainable Microbial and Biocatalytic Production of Advanced
Functional Materials” (BIOPRODUCTION/NMP-2-T-2007-026515)
funded by the European Commission.
The research has been also supported by a Marie Curie Action
RTN, Biocatalytic Approach to Material Design BIOMADE (D.P., Con-
tract No. MRTN-CT-2004-505147).
Richard Hoogenboom is grateful to the Alexander von Humboldt
foundation and the Netherlands Scientific Organisation (NWO) for
financial support.
References
[1] E.S. Gil, S.A. Hudson, Prog. Polym. Sci. 29 (2004) 1173–1222.
[2] B.R. Twaites, C.D. Alarcon, D. Cunliffe, M. Lavigne, S. Pennadam, J.R. Smith, D.C.
Gorecki, C. Alexander, J. Control. Release 97 (2004) 551–566.
[3] J.F. Kunzler, J.A. McGee, Chem. Ind. (1995) 651–655.
[4] D. Schmaljohann, Adv. Drug Deliv. Rev. 58 (2006) 1655–1670.
[5] J.T. Zhang, Y.N. Xue, F.Z. Gao, S.W. Huang, R.X. Zhuo, J. Appl. Polym. Sci. 108
(2008) 3031–3037.
[6] M. Kurisawa, M. Yokoyama, T. Okano, J. Control. Release 69 (2000) 127–137.
[7] J.V.M. Weaver, I. Bannister, K.L. Robinson, X. Bories-Azeau, S.P. Armes, M. Small-
ridge, P. McKenna, Macromolecules 37 (2004) 2395–2403.
[8] T.M. Eggenhuisen, C.R. Becer, M.W.M. Fijten, R. Eckardt, R. Hoogenboom, U.S.
Schubert, Macromolecules 41 (2008) 5132–5140.
[42] W. Du, L. Wang, D.H. Liu, Green Chem. 9 (2007) 173–176.
[43] S. Chand, P. Adlercreutz, B. Mattiasson, Enzyme Microb. Technol. 20 (1997)
102–106.
[44] J.E. Puskas, M.Y. Sen, J.R. Kasper, J. Polym. Sci. Polym. Chem. 46 (2008)
3024–3028.
[45] H.E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 62 (1997) 7512–7515.
[46] K.L. Deng, H. Tian, P.F. Zhang, X.B. Ren, H.B. Zhong, Express. Polym. Lett. 3 (2009)
97–104.
[9] M. Save, J.V.M. Weaver, S.P. Armes, P. McKenna, Macromolecules 35 (2002)
1152–1159.
[47] I. Hilker, G. Rabani, G.K.M. Verzijl, A.R.A. Palmans, A. Heise, Angew. Chem.-Int.
Ed. 45 (2006) 2130–2132.
[10] M.T. Iglesias, J. Guzman, E. Riande, J. Polym. Sci. Polym. Chem. 32 (1994)
2565–2576.
[48] V. Leonard, L. Fransson, S. Lamare, K. Hult, M. Graber, ChemBioChem 8 (2007)
662–667.
[11] M.T. Iglesias, J. Guzman, E. Riande, J. Polym. Sci. Polym. Chem. 33 (1995)
2057–2067.
[49] V. Leonard-Nevers, Z. Marton, S. Lamare, K. Hult, M. Graber, J. Mol. Catal. B-
Enzym. 59 (2009) 90–95.
[12] F. Garcia, J.L. De la Pena, J.J. Delgado, N. Garcia, J. Guzman, E. Riande, P. Calle, J.
Polym. Sci. Polym. Chem. 39 (2001) 1843–1853.