Synthesis of enantiomerically pure glycidol via a fully enantioselective lipase-catalyzed resolution

Tetrahedron Asymmetry

Volumn 16, Issue 4, 2005, Pages 869-874

  Palomo, Jose M ^a   Segura, Rosa L ^a   Mateo, Cesar ^a   Terreni, Marco ^b   Guisan, José M ^a   Fernández Lafuente, Roberto ^a  

^a CSIC   (Spain)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIETHYLAMINOETHANOL; BUTYRIC ACID DERIVATIVE; DIOXANE; GLYCIDOL; GLYCIDYL BUTYRATE; SEPHAROSE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOCATALYST; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME PURIFICATION; EXTRACTION; HYDROLYSIS; IMMOBILIZATION; LOW TEMPERATURE; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; SWINE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 13844256708     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.12.027     Document Type: Article

References (33)

1. J.A.M. de Bont Tetrahedron: Asymmetry 4 1993 1331 1340
2. N. Kasai, T. Suzuki, and Y. Furukawa J. Mol. Catal. B: Enzym. 4 1998 237 252
3. D.J. Leak, P.J. Aikens, and M. Seyed-Mahmoudian Trends Biotechnol. 10 1992 256
4. C.H. Heathcock, M. McLaughlin, J. Medina, J.L. Hubbs, G.A. Wallace, R. Scott, M.M. Claffey, C.J. Hayes, and G.R. Ott J. Am. Chem. Soc. 125 2003 12844 12849
5. Y. Kiyotsuka, J. Igarashi, and Y. Kobayashi Tetrahedron Lett. 43 2002 2725 2729
6. J. Wouters, F. Moureau, G. Evrard, J.J. Koenig, S. Jegham, P. Gorge, and F. Durant Bioorg. Med. Chem. 7 1999 1683 1693
7. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
8. M. Caron, and K.B. Sharpless J. Org. Chem. 50 1985 1560 1563
9. J.M. Klunder, S.Y. Ko, and K.B. Sharpless J. Org. Chem. 51 1986 3710
10. L.P.C. Nielsen, C.P. Stevenson, D.G. Blackmond, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 1360 1362
11. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315 and references cited therein
12. J.H. Brown Tetrahedron: Asymmetry 2 1991 481
13. W.E. Ladner, and G. Whitesides J. Am. Chem. Soc. 106 1984 7251
14. Z. Wang, J. Quan, L. Weng, X.-j. Gou, J. Ma, G. Zhang, and S. Cao Jilin Daxue Xuebao, Lixueban. 41 2003 213 216
15. S. Jia, J. Xu, Q. Li, and J. Yu Appl. Biochem. Biotech. 104 2003 69 79
16. J.M. Palomo, R.L. Segura, G. Fernández-Lorente, J.M. Guisán, and R. Fernández-Lafuente Tetrahedron: Asymmetry 15 2004 1157 1161
17. M. Kloosterman, V.H.M. Elferink, J van. Iersel, J.-H. Roskam, E.M. Meijer, A. Hulshof, and R.A. Sheldon TIBTECH. 6 1988 251
18. Jose M. Palomo, G. Fernandez-Lorente, M.L. Rua, J.M. Guisan, and R. Fernandez-Lafuente Tetrahedron: Asymmetry 14 2003 3679 3687
19. J.M. Palomo, G. Fernandez-Lorente, C. Mateo, M. Fuentes, R. Fernandez-Lafuente, and J.M. Guisan Tetrahedron: Asymmetry 13 2002 1337 1345
20. J.M. Palomo, G. Fernández-Lorente, G. Muñoz, C. Mateo, M. Fuentes, J.M. Guisán, and R. Fernández-Lafuente J. Mol. Catal. B: Enzym. 21 2003 201 210
21. Jose M. Palomo, G. Fernández-Lorente, C. Mateo, C. Ortiz, R. Fernández-Lafuente, and J.M. Guisán Enzyme. Microb. Technol. 31 2002 775 783
22. D. Ghosh, Z. Wawrzak, V.Z. Pletnev, N. Li, R. Kaiser, W. Pangborn, H. Jomvall, M. Erman, and W.L. Duax Structure 3 1995 279 288
23. L. Brady, A.M. Brzozowski, Z.S. Derewenda, E. Dodson, G. Dodson, S. Tolley, J.P. Turkenburg, L. Christiansen, B. Huge-Jensen, L. Norskov, L. Thim, and U. Menge Nature 343 1990 767 770
24. L. Sarda, and P. Desnuelle Biochim. Biophys. Acta 30 1958 513 521
25. U. Derewenda, A.M. Brzozowski, D.M. Lawson, and Z.S. Derewenda Biochemistry 31 1992 1532 1541
26. R.L. Segura, J.M. Palomo, C. Mateo, M. Terreni, Jose M. Guisán, and R. Fernández-Lafuente Biotechnol. Prog. 30 2004 825 829
27. Segura, R. L.; Betancor, L.; Palomo, J. M.; Hidalgo, A.; Fernandez-Lorente, G.; Terreni, M.; Mateo, C.; Cortés, A.; Fernández-Lafuente, R.; Guisán, J. M. Biomacromolecules, submitted for publication
28. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
29. R. Fernandez-Lafuente, C.M. Rosell, V. Rodriguez, C. Santana, G. Soler, A. Bastida, and J.M. Guisan Enzyme Microb. Technol. 15 1993 546 550
30. R. Fernandez-Lafuente, V. Rodriguez, and J.M. Guisan Enzyme. Microb. Technol. 23 1998 28 33
31. M.M. Bradford Anal. Biochem. 72 1976 248 254
32. A. Bastida, P. Sabuquillo, P. Armisen, R. Fernández-Lafuente, J. Huguet, and J.M. Guisán Biotechnol. Bioeng. 58 1998 486 493
33. M. Fuentes, B.C.C. Pessela, J.V. Maquiese, C. Ortiz, R.L. Segura, Jose M. Palomo, O. Abian, J.M. Guisán, C. Mateo, and R. Fernández- Lafuente Biotechnol. Prog. 30 2004 1134 1139