Highly enantioselective acylation of chlorohydrins using Amano AK lipase from P. fluorescens immobilized on silk fibroin-alginate spheres

Tetrahedron Letters

Volumn 55, Issue 36, 2014, Pages 5062-5065

  Ferreira, Irlon M ^a   Nishimura, Rodolfo H V ^a   Souza, Ana B Dos A ^a   Clososki, Giuliano C ^a   Yoshioka, Sergio A ^a   Porto, André L M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Biocatalysis; Chiral chlorohydrins; Enzymatic kinetic resolution; Pseudomonas fluorescens; Silk fibroin

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALGINIC ACID; CHLOROHYDRIN DERIVATIVE; SILK FIBROIN;

ACYLATION; ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; NONHUMAN; PSEUDOMONAS FLUORESCENS; SYNTHESIS;

PSEUDOMONAS FLUORESCENS;

EID: 84906960202     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.07.032     Document Type: Article

References (37)

1. P.J. Dunn Chem. Soc. Rev. 41 2012 1452 1461
2. R. Cirminna, and M. Pagliaro Org. Process Res. Dev. 17 2013 1479 1484
3. A. Kamal, and G. Chouhan Tetrahedron Lett. 45 2004 8801 8805
4. P.K. Dhake, D.D. Thakare, and M.B. Bhanage Flavour Gragr. J. 28 2013 71 83
5. R.E. Deasy, T.S. Mood, and A.R. Maguire Tetrahedron: Asymmetry 24 2013 1480 1487
6. Z.B. Xie, N. Wang, G.F. Jiang, and X.Q. Yu Tetrahedron Lett. 54 2013 945 948
7. J.L. Ramos, W. Neto, and J.M. Woodley Top. Catal. 57 2014 301 320
8. Y. Fan, and J. Qian J. Mol. Catal. B: Enzym. 66 2010 1 7
9. C. Raminelli, A. dos Santos, A.L.M. Porto, L.H. Andrade, and J.V. Comasseto Tetrahedron 61 2005 409 415
10. R.A. Sheldon, and D.V. Pelt Chem. Soc. Rev. 42 2013 6223 6235
11. C.G.C.M. Netto, L.H. Andrade, and H.E. Toma Tetrahedron: Asymmetry 20 2009 2299 2304
12. L.P. Rebelo, C.G.C.M. Netto, H.E. Toma, and L.H. Andrade J. Braz. Chem. Soc. 21 2010 1537 1542
13. A.S. Bommarius, and M.F. Paye Chem. Soc. Rev. 42 2013 6534 6565
14. W.G. Huisman, and J.S. Collier Curr. Opin. Chem. Biol. 17 2013 284 292
15. P. Adlercreutz Chem. Soc. Rev. 42 2013 6406 6436
16. R. DiCosimo, J. McAuliffe, A.J. Poulose, and G. Bohlmann Chem. Soc. Rev. 42 2013 6437 6474
17. R.C. Rodrigues, C. Ortiz, A.C. Murcia, R. Torres, and R.F. Lafuente Chem. Soc. Rev. 42 2013 6290 6307
18. X.-J. Huang, D. Ge, and Z.-K. Xu Eur. Polym. J. 43 2007 3710 3718
19. B. Chen, C. Yin, Y. Cheng, W. Li, Z.-a. Cao, and T. Tan Biomass Bioenergy 39 2012 59 66
20. L.C. Rocha, A.L. de Souza, U.P.R. Filho, S.P.C. Filho, L.D. Setteb, and A.L.M. Porto J. Mol. Catal. B: Enzym. 84 2012 160 165
21. Y. Zhang Biotechnol. Adv. 20 2002 91
22. E. Bini, D. Knight, and D. Kaplan J. Mol. Biol. 335 2004 27 40
23. M.A. Moraes, R.F. Weska, and M.M.J. Beppu Biomed. Mater. Res. B Appl. Biomater. 102 2014 869
24. C. Foo, E. Bini, J. Huang, S. Lee, and D. Kaplan Appl. Phys. A Mater. Sci. Process. 82 2006 193 203
25. M. Wang, H. Jin, D. Kaplan, and G. Rutledge Macromolecules 37 2004 6856 6864
26. M. Bergeron-Brlek, T. Teoh, and R. Britton Org. Lett. 15 2013 3554 3557
27. J. Zhang, J. Wang, Z. Qiu, and Y. Wang Tetrahedron 67 2011 6859 6887
28. A.P. Bentley, Y. Mei, and J. Du Tetrahedron Lett. 49 2008 1425 1427
29. Y.M.K. Usami J. Nat. Prod. 74 2011 877 881
30. D.M. Hodgson, S. Salik, and D. Fox J. Org. Chem. 75 2010 2157 2168
31. J. Hiratake, M. Inagaki, T. Nishioka, and J. Oda J. Org. Chem. 53 1988 6130 6133
32. A. Träff, K. Bogá, M. Warner, and Jan-E. Bäckvall Org. Lett. 10 2008 4807 4810
33. W.-J. Zhou, Y. Ni, G.-W. Zheng, H.-H. Chen, Z.-R. Zhu, and J.-H. Xu J. Mol. Catal. B: Enzym. 99 2014 102 107
34. R.H.V. Nishimura, F.T. Toledo, J.L.C. Lopes, and G.C. Clososki Tetrahedron Lett. 54 2013 287 290
35. J.B. Reigada, C.M. Tcacenco, L.H. Andrade, M.J. Kato, A.L.M. Porto, and J.H.G. Lago Tetrahedron: Asymmetry 18 2007 1054 1058
36. S. Sakai, Y. Liu, R. Watanabe, M. Kawabe, M. Taya, and K. Kawakami J. Mol. Catal. B: Enzym. 83 2012 120 124
37. K. Faber Biotransformation in Organic Chemistry 4th ed. 2000 Springer Berlin