Chemoenzymatic epoxidation of alkenes based on peracid formation by a Rhizomucor miehei lipase-catalyzed perhydrolysis reaction

Tetrahedron

Volumn 70, Issue 6, 2014, Pages 1144-1148

  Méndez Sánchez, Daniel ^a   Ríos Lombardía, Nicolás ^a   Gotor, Vicente ^a   Gotor Fernández, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkenes; Biocatalysis; Epoxidation; Hydrolases; Rhizomucor miehei lipase

Indexed keywords

1,2 DIHYDRONAPHTHALENE; 1,4 DIHYDRONAPHTHALENE; 2 BROMOSTYRENE; 2 METHYLCYCLOHEXENE; 3 BROMOSTYRENE; 4 BROMOSTYRENE; 4 OCTENE; ALKENE DERIVATIVE; CARBOXYLIC ACID; CARVONE; CYCLOHEPTENE; CYCLOHEXENE; CYCLOHEXENE DERIVATIVE; EPOXIDE; HYDROGEN PEROXIDE; LAURIC ACID; LIMONENE; NAPHTHALENE DERIVATIVE; PERACID; PEROXY RADICAL; STYRENE; STYRENE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMOENZYMATIC EPOXIDATION; EPOXIDATION; GAS CHROMATOGRAPHY; LIPID HYDROLYSIS; NONHUMAN; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; RHIZOMUCOR MIEHEI; THERMOSTABILITY;

RHIZOMUCOR MIEHEI;

EID: 84892830091     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.12.084     Document Type: Article

References (47)

1. K. Matsumoto, T. Katsuki, and I.W.C.E. Arends J.G. de Vries, G.A. Molander, P.A. Evans, Science of Synthesis, Stereoselective Synthesis Vol. 1 2011 Thieme Sttutgart, Germany 69 121
2. V.B. Urlacher, and M. Girhard Trends Biotechnol. 30 2012 26 36
3. S.A. Hauser, M. Gokoja, and F.E. Kühn Catal. Sci. Technol. 3 2013 552 561
4. K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2024 2032
5. I.W.C.E. Arends Angew. Chem., Int. Ed. 45 2006 6250 6252
6. D. Díez, M.G. Nunez, A.B. Antón, R.F. Moro, N.M. Garrido, I.S. Marcos, P. Basabe, and J.G. Urones Curr. Org. Synth. 5 2008 186 216
7. Y. Shi J.-E. Bäckvall, Modern Oxidation. Methods 2010 Wiley-VCH Weinheim, Germany 85 115
8. G.-D. Roiban, R. Agudo, and M.T. Reetz Tetrahedron 69 2013 5306 5311
9. A. Li, J. Liu, S.Q. Pham, and Z. Li Chem. Commun. 2013 11572 11574
10. R.D. Schmid, and V.B. Urlacher Modern Biooxidation. Enzymes, Reactions and Applications 2007 Wiley-VCH Weinheim, Germany
11. D. Yin, Q. Jing, W.W. Aldajani, S. Duncan, U. Tschirner, J. Schilling, and R.J. Kazlauskas Bioresour. Technol. 102 2011 5183 5192
12. D. Gamenara, G.A. Seoane, P. Saenz-Méndez, and P. Domínguez de María Redox Biocatalysis: Fundamental and Applications 2012 John Wiley & Sons Hoboken, NJ
13. L. Wiermans, S. Hofzumahaus, C. Schotten, L. Weigand, A. Schallmey, and P. Domínguez de María ChemCatChem 5 2013 3719 3724
14. D. Yin, V.M. Purpero, R. Fujii, Q. Jing, and R.J. Kazlauskas Chem. - Eur. J. 19 2013 3037 3046
15. F. Björkling, A.E. Godtfredsen, and O. Kirk J. Chem. Soc., Chem. Commun. 1990 1301 1303
16. Carboni-Oerlemans, P. Domínguez de María, B. Tuin, G. Bageman, A. van der Meer, and van Gemert J. Mol. Catal. B: Enzym. 126 2006 140 151
17. C. Orellana-Coca, J.M. Billakanti, B. Mattiason, and R. Hatti-Kaul J. Mol. Catal. B: Enzym. 44 2007 133 137
18. A.J. Kotlewska, F. van Rantwijk, R.A. Sheldon, and I.W.C.E. Arends Green Chem. 13 2011 2154 2160
19. G. Chávez, R. Hatti-Kaul, R.A. Sheldon, and G. Mamo J. Mol. Catal. B: Enzym. 89 2013 67 72
20. L. Wiermans, M. Pérez-Sánchez, and P. Domínguez de María ChemSusChem 6 2013 251 255
21. U.T. Bornscheuer, and R.J. Kazlauskas Angew. Chem., Int. Ed. 43 2004 6032 6040
22. K. Hult, and P. Berglund Trends Biotechnol. 25 2007 231 238
23. A. Babtie, N. Tokuriti, and F. Hollfelder Curr. Opin. Chem. Biol. 14 2010 200 207
24. E. Busto, V. Gotor-Fernández, and V. Gotor Chem. Soc. Rev. 39 2010 4504 4523
25. Q. Wu, B.-K. Liu, and X.F. Lin Curr. Org. Chem. 14 2010 1966 1988
26. M.S. Humble, and P. Berglund Eur. J. Org. Chem. 2011 3391 3401
27. K. Sarma, N. Bhati, N. Borthakur, and A. Goswami Tetrahedron 63 2007 8735 8741
28. K. Sarma, A. Goswami, and B.C. Goswami Tetrahedron: Asymmetry 20 2009 1295 1300
29. M. Svedendahl, P. Carlqvist, C. Branneby, O. Allnér, A. Frise, K. Hult, P. Berglund, and T. Brinck ChemBioChem 9 2008 2443 2451
30. M.R. gen Klaas, and S. Warwel J. Mol. Catal. A: Chem. 117 1997 311 319
31. A.W.:P. Jarvie, N. Overton, and C.B. St Pourçain Chem. Commun. 1998 177 178
32. M.R. gen Klaas, and S. Warwel Org. Lett. 1 1999 1025 1026
33. A.W.P. Jarvie, N. Overton, and C.B. St Pourçain J. Chem. Soc., Perkin Trans. 1 1999 2171 2176
34. R.M. Lau, F. van Rantwijk, and R.A. Sheldon Org. Lett. 2 2000 4189 4191
35. I. Hilker, D. Bothe, J. Prüss, and H.-J. Warnecke Chem. Eng. Sci. 56 2001 427 432
36. H. Uyama, M. Kuwabara, T. Tsujimoto, and S. Kobayashi Biomacromolecules 4 2003 211 215
37. E.G. Ankudey, H.F. Olivo, and T.L. Peeples Green Chem. 8 2006 923 926
38. P. Tufvesson, D. Adlecreutz, S. Lundmark, M. Manea, and R. Hatti-Kaul J. Mol. Catal. B: Enzym. 54 2008 1 6
39. C. Wiles, M.J. Hammond, and P. Watts Belstein J. Org. Chem. 5 2009 27 10.3762/bjoc.5.27
40. Y. Xu, N.R.B.J. Khaw, and Z. Li Green Chem. 11 2009 2047 2051
41. F.A. Corrêa, F.K. Sutili, L.S.M. Miranda, S.G.F. Leite, R.O.M.A. de Souza, and I.C.R. Leal J. Mol. Catal. B: Enzym. 81 2012 7 11
42. M.A. Moreira, T.B. Bitencourt, and M.G. Nascimiento Synth. Commun. 35 2005 2107 2114
43. R.C. Rodrigues, and R. Fernández-Lafuente J. Mol. Catal. B: Enzym. 64 2010 1 22
44. F. Björkling, H. Frykman, A.E. Godtfredsen, and O. Kirk Tetrahedron 48 1992 4587 4592
45. V. Skouridou, H. Stamatis, and F.N. Kolisis J. Mol. Catal. B: Enzym. 21 2003 67 69
46. V. Skouridou, H. Stamatis, and F.N. Kolisis Biocatal. Biotransform. 21 2003 285 290
47. M.A. Moreira, and M.G. Nascimento Catal. Commun. 8 2007 2043 2047