Hydroxy functional acrylate and methacrylate monomers prepared via lipase-catalyzed transacylation reactions

Journal of Molecular Catalysis B: Enzymatic

Volumn 62, Issue 1, 2010, Pages 80-89

  Popescu, Dragos ^a   Hoogenboom, Richard ^a   Keul, Helmut ^a   Moeller, Martin ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Candida antarctica lipase B; Enzyme catalyzed transacylation; Functional monomers

Indexed keywords

2-METHYL-2-BUTANOL; ACYL DONORS; ACYLATED PRODUCTS; CANDIDA ANTARCTICA LIPASE B; CATALYZED REACTIONS; ENZYME-CATALYZED TRANSACYLATION; EXPERIMENTAL CONDITIONS; FUNCTIONAL MONOMER; HIGH YIELD; HYDROXYL GROUPS; METHACRYLATE MONOMERS; METHYL ACRYLATES; METHYL METHACRYLATES; NOVOZYME 435; REACTION CONDITIONS;

ENZYMES; ESTERS; FLUORINE CONTAINING POLYMERS; MONOMERS; ORGANIC POLYMERS;

ISOMERS;

ACRYLIC ACID; ACRYLIC ACID METHYL ESTER; HYDROXYL GROUP; LIPASE B; METHACRYLIC ACID; METHACRYLIC ACID METHYL ESTER; METHANOL; MONOMER; THIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

CANDIDA ANTARCTICA;

EID: 71549169271     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2009.09.008     Document Type: Article

References (49)

1. Gil E.S., and Hudson S.A. Prog. Polym. Sci. 29 (2004) 1173-1222
2. Twaites B.R., Alarcon C.D., Cunliffe D., Lavigne M., Pennadam S., Smith J.R., Gorecki D.C., and Alexander C. J. Control. Release 97 (2004) 551-566
3. Kunzler J.F., and McGee J.A. Chem. Ind. (1995) 651-655
4. Schmaljohann D. Adv. Drug Deliv. Rev. 58 (2006) 1655-1670
5. Zhang J.T., Xue Y.N., Gao F.Z., Huang S.W., and Zhuo R.X. J. Appl. Polym. Sci. 108 (2008) 3031-3037
6. Kurisawa M., Yokoyama M., and Okano T. J. Control. Release 69 (2000) 127-137
7. Weaver J.V.M., Bannister I., Robinson K.L., Bories-Azeau X., Armes S.P., Smallridge M., and McKenna P. Macromolecules 37 (2004) 2395-2403
8. Eggenhuisen T.M., Becer C.R., Fijten M.W.M., Eckardt R., Hoogenboom R., and Schubert U.S. Macromolecules 41 (2008) 5132-5140
9. Save M., Weaver J.V.M., Armes S.P., and McKenna P. Macromolecules 35 (2002) 1152-1159
10. Iglesias M.T., Guzman J., and Riande E. J. Polym. Sci. Polym. Chem. 32 (1994) 2565-2576
11. Iglesias M.T., Guzman J., and Riande E. J. Polym. Sci. Polym. Chem. 33 (1995) 2057-2067
12. Garcia F., De la Pena J.L., Delgado J.J., Garcia N., Guzman J., Riande E., and Calle P. J. Polym. Sci. Polym. Chem. 39 (2001) 1843-1853
13. Woundenberg-Van Oosterom M., Van Rantwijk F., and Sheldon R.A. Biotechnol. Bioeng. 49 (1996) 328-333
14. Jing Q., and Kaziauskas R.J. Chirality 20 (2008) 724-735
15. Gadler P., and Faber K. Trends Biotechnol. 25 (2007) 83-88
16. Du W., Xu Y.Y., Liu D.H., and Li Z.B. J. Mol. Catal. B-Enzym. 37 (2005) 68-71
17. Iso M., Chen B.X., Eguchi M., Kudo T., and Shrestha S. J. Mol. Catal. B-Enzym. 16 (2001) 53-58
18. Yang J.S., Jeon G.J., Hur B.K., and Yang J.W. J. Microbiol. Biotechnol. 15 (2005) 1183-1188
19. Bloomer S., Adlercreutz P., and Mattiasson B. Enzyme Microb. Technol. 14 (1992) 546-552
20. Li Z.Y., and Ward O.P. J. Am. Oil Chem. Soc. 70 (1993) 745-748
21. Popescu D., Keul H., and Moeller M. Macromol. Chem. Phys. 210 (2009) 123-139
22. Sen M.Y., Puskas J.E., Ummadisetty S., and Kennedy J.P. Macromol. Rapid Commun. 29 (2008) 1598-1602
23. Ramaswamy S., Morgan B., and Oehlschlager A.C. Tetrahedron Lett. 31 (1990) 3405-3408
24. Li X.F., Zong M.H., and Yang R.D. J. Mol. Catal. B-Enzym. 38 (2006) 48-53
25. Chan A.W.-Y., and Ganem B. Biocatal. Biotransform. 8 (1993) 163-169
26. Hajjar A.B., Nicks P.F., and Knowles C. J. Biotechnol. Lett. 12 (1990) 825-830
27. Ikeda I., Tanaka J., and Suzuki K. Tetrahedron Lett. 32 (1991) 6865-6866
28. Derango R., Wang Y.F., Dowbenko R., and Chiang L.C. Biotechnol. Lett. 16 (1994) 241-246
29. Warwel S., Steinke G., Rusch A., and Klaas M.R. Biotechnol. Technol. 10 (1996) 283-286
30. Athawale V., Manjrekar N., and Athawale M. Tetrahedron Lett. 43 (2002) 4797-4800
31. G. Burghard, H. Geoffrey (invs.), Goldschmidt GmbH, EP 0965645B1, 1999.
32. Kobayashi S., Uyama H., and Kimura S. Chem. Rev. 101 (2001) 3793-3818
33. Gross R.A., Kumar A., and Kalra B. Chem. Rev. 101 (2001) 2097-2124
34. Binns F., Harffey P., Roberts S.M., and Taylor A. J. Chem. Soc.-Perkin Trans. 1 (1999) 2671-2676
35. Anderson E.M., Karin M., and Kirk O. Biocatal. Biotransform. 16 (1998) 181-204
36. Hans M., Keul H., Heise A., and Moeller M. Macromolecules 40 (2007) 8872-8880
37. Ferrer M., Soliveri J., Plou F.J., Lopez-Cortes N., Reyes-Duarte D., Christensen M., Copa-Patino J.L., and Ballesteros A. Enzyme Microb. Technol. 36 (2005) 391-398
38. Chamouleau F., Coulon D., Girardin M., and Ghoul M. J. Mol. Catal. B-Enzym. 11 (2001) 949-954
39. Watanabe Y., Shimada Y., Sugihara A., Noda H., Fukuda H., and Tominaga Y. J. Am. Oil Chem. Soc. 77 (2000) 355-360
40. Soumanou M.M., and Bornscheuer U.T. Enzyme Microb. Technol. 33 (2003) 97-103
41. Watanabe Y., Shimada Y., Sugihara A., and Tominaga Y. J. Am. Oil Chem. Soc. 78 (2001) 703-707
42. Du W., Wang L., and Liu D.H. Green Chem. 9 (2007) 173-176
43. Chand S., Adlercreutz P., and Mattiasson B. Enzyme Microb. Technol. 20 (1997) 102-106
44. Puskas J.E., Sen M.Y., and Kasper J.R. J. Polym. Sci. Polym. Chem. 46 (2008) 3024-3028
45. Gottlieb H.E., Kotlyar V., and Nudelman A. J. Org. Chem. 62 (1997) 7512-7515
46. Deng K.L., Tian H., Zhang P.F., Ren X.B., and Zhong H.B. Express. Polym. Lett. 3 (2009) 97-104
47. Hilker I., Rabani G., Verzijl G.K.M., Palmans A.R.A., and Heise A. Angew. Chem.-Int. Ed. 45 (2006) 2130-2132
48. Leonard V., Fransson L., Lamare S., Hult K., and Graber M. ChemBioChem 8 (2007) 662-667
49. Leonard-Nevers V., Marton Z., Lamare S., Hult K., and Graber M. J. Mol. Catal. B-Enzym. 59 (2009) 90-95