Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study

Journal of Molecular Catalysis B: Enzymatic

Volumn 98, Issue , 2013, Pages 21-29

  Escorcia, Andrés M ^a   Molina, Daniel ^a   Daza, Martha C ^a   Doerr, Markus ^a,b  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD SANTO TOMÁS   (Colombia)

Author keywords

Candida antarctica lipase B; Chemoselectivity; Chiral resolution; Molecular modeling; NMR spectroscopy

Indexed keywords

CANDIDA ANTARCTICA LIPASE B; CHEMO-SELECTIVITY; CHIRAL RESOLUTIONS; COMPUTATIONAL STUDIES; ENZYME PURIFICATION; METHANOL CONCENTRATION; MOLECULAR DOCKING; POOR SOLUBILITIES;

ACETYLATION; BINDING ENERGY; CATALYSIS; ISOMERS; METHANOL; MOLECULAR DYNAMICS; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; STEREOCHEMISTRY; TOLUENE;

ENANTIOSELECTIVITY;

DRUG SOLVENT; LIPASE B; METHANOL; PROPRANOLOL; TOLUENE; VINYL ACETATE;

ALCOHOLYSIS; ARTICLE; BINDING AFFINITY; CANDIDA ANTARCTICA; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ACETYLATION; DRUG SOLUBILITY; ENANTIOSELECTIVITY; ENZYME PURIFICATION; HYDROLYSIS; MICHAELIS CONSTANT; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR MODEL; NONHUMAN; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE;

CANDIDA ANTARCTICA;

EID: 84885363859     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2013.09.019     Document Type: Article

References (82)

1. A.M. Barret J. Pharmacol. 16 1985 95 108
2. R. Rabkin, D.P. Stables, N.W. Levin, and M.M. Suzman Am. J. Cardiol. 18 1966 370 380
3. E.M. Besterman, and D.H. Friedlander Postgrad. Med. J. 41 1965 526 535
4. C.V.S. Ram Am. J. Cardiol. 102 2008 242 244
5. S. Belknap Evid. Based. Med. 13 2008 50
6. D. Patakas, V. Argiropoulou, G. Louridas, and V. Tsara Thorax 38 1983 108 112
7. H.S. Bevinakatti, and A.A. Banerji J. Org. Chem. 56 1991 5372 5375
8. S.V. Darnle, P.N. Patil, and M.M. Salunkhe Synth. Commun. 29 1999 3855 3862
9. A. Kamal, M. Sandbhor, and A. Ali Shaik Bioorg. Med. Chem. Lett. 14 2004 4581 4583
10. R.A. Veloo, and G.-J. Koomen Tetrahedron: Asymmetry 4 1993 2401 2404
11. H. Sasai, N. Itoh, T. Suzuki, and M. Shibasaki Tetrahedron Lett. 34 1993 855 858
12. Y.-F. Wang, S.-T. Chen, K.K.-C. Liu, and C.-H. Wong Tetrahedron Lett. 30 1989 1917 1920
13. O. Barbosa, C. Ariza, C. Ortiz, and R. Torres New Biotechnol. 27 2010 844 850
14. T.-W. Chiou, C.-C. Chang, C.-T. Lai, and D.-F. Tai Bioorg. Med. Chem. Lett. 7 1997 433 436
15. R. Ávila-González, M. Pérez-Gilabert, and F. García-Carmona J. Biosci. Bioeng. 100 2005 423 428
16. R. Ávila, R. Ruiz, D. Amaro-González, O. Díaz, J.A. González, and A.J. Núñez Lat. Am. Appl. Res. 35 2005 307 311
17. V. Gotor-Fernández, R. Brieva, and V. Gotor J. Mol. Catal. B: Enzym. 40 2006 111 120
18. A. Ghanem, and H.Y. Aboul-Enein Tetrahedron: Asymmetry 15 2004 3331 3351
19. A. Ghanem Tetrahedron 63 2007 1721 1754
20. M.T. Reetz Curr. Opin. Chem. Biol. 6 2002 145 150
21. M. Romero, J. Gomez, B. Diaz-Suelto, A. Garcia-Sanz, and N. Baster Appl. Biochem. Biotechnol. 165 2011 1129 1140
22. M. Rodríguez-Mata, V. Gotor-Fernández, J. González-Sabín, F. Rebolledo, and V. Gotor Org. Biomol. Chem. 9 2011 2274 2278
23. D. Brady, S. Reddy, B. Mboniswa, L.H. Steenkamp, A.L. Rousseau, C.J. Parkinson, J. Chaplin, R.K. Mitra, T. Moutlana, S.F. Marais, and N.S. Gardiner J. Mol. Catal. B: Enzym. 75 2012 1 10
24. O. Barbosa, C. Ortiz, R. Torres, and R. Fernandez-Lafuente J. Mol. Catal. B: Enzym. 71 2011 124 132
25. V. Léonard-Nevers, Z. Marton, S. Lamare, K. Hult, and M. Graber J. Mol. Catal. B: Enzym. 59 2009 90 95
26. B. Gao, T. Xu, J. Lin, L. Zhang, E. Su, Z. Jiang, and D. Wei J. Mol. Catal. B: Enzym. 68 2011 286 291
27. M. Maciejewski, K. Półtorak, and J.E. Kamińska J. Mol. Catal. B: Enzym. 62 2010 248 256
28. S. Serra Tetrahedron: Asymmetry 22 2011 619 628
29. N. Li, S.-B. Hu, and G.-Y. Feng Biotechnol. Lett. 34 2012 153 158
30. L. Piovan, M.D. Pasquini, and L.H. Andrade Molecules 16 2011 8098 8109
31. C. Pilissão, P.de O. Carvalho, and M da G. Nascimento Process Biochem. 44 2009 1352 1357
32. J.B. Sontakke, and G.D. Yadav J. Chem. Technol. Biotechnol. 86 2011 739 748
33. F. van Rantwijk, and R.A. Sheldon Tetrahedron 60 2004 501 519
34. J.A. Rodríguez-Rodríguez, F.J. Quijada, R. Brieva, F. Rebolledo, and V. Gotor Tetrahedron 69 2013 5407 5412
35. F. Le Joubioux, N. Bridiau, Y. Ben Henda, O. Achour, M. Graber, and T. Maugard J. Mol. Catal. B: Enzym. 95 2013 99 110
36. E. Husson, V. Garcia-Matilla, C. Humeau, I. Chevalot, F. Fournier, and I. Marc Enzyme Microb. Technol. 46 2010 338 346
37. L. Schönstein, E. Forró, and F. Fülöp Tetrahedron: Asymmetry 24 2013 202 206
38. K. Lundell, E. Katainen, A. Kiviniemi, and L.T. Kanerva Tetrahedron: Asymmetry 15 2004 3723 3729
39. F. Le Joubioux, Y.B. Henda, N. Bridiau, O. Achour, M. Graber, and T. Maugard J. Mol. Catal. B: Enzym. 85/86 2013 193 199
40. M. Fernández-Pérez, and C. Otero Enzyme Microb. Technol. 33 2003 650 660
41. L.T. Kanerva, E. Vänttinen, T.T. Huuhtanen, and M. Dahlqvist Acta Chem. Scand. 46 1992 1101 1105
42. T. Furutani, M. Furui, H. Ooshima, and J. Kato Enzyme Microb. Technol. 19 1996 578 584
43. P.-O. Syrén, F. Le Joubioux, Y. Ben Henda, T. Maugard, K. Hult, and M. Graber ChemCatChem 5 2013 1842 1853
44. E. Husson, C. Humeau, F. Blanchard, X. Framboisier, I. Marc, and I. Chevalot J. Mol. Catal. B: Enzym. 55 2008 110 117
45. D. Yildirim, and S.S. Tükel Process Biochem. 48 2013 819 830
46. J. Quan, N. Wang, X.-Q. Cai, Q. Wu, and X.-F. Lin J. Mol. Catal. B: Enzym. 44 2007 1 7
47. C. Oger, Z. Marton, Y. Brinkmann, V. Bultel-Poncé, T. Durand, M. Graber, and J.-M. Galano J. Org. Chem. 75 2010 1892 1897
48. H. Zhou, J. Chen, L. Ye, H. Lin, and Y. Yuan Bioresour. Technol. 102 2011 5562 5566
49. J. Nyhlén, B. Martín-Matute, A.G. Sandström, M. Bocola, and J. Bäckvall ChemBioChem 9 2008 1968 1974
50. M.T. Reetz, M. Puls, J.D. Carballeira, A. Vogel, K. Jaeger, T. Eggert, W. Thiel, M. Bocola, and N. Otte ChemBioChem 8 2007 106 112
51. S.A. Funke, N. Otte, T. Eggert, M. Bocola, K.-E. Jaeger, and W. Thiel Protein Eng. Des. Sel. 18 2005 509 514
52. M. Bocola, N. Otte, K. Jaeger, M.T. Reetz, and W. Thiel ChemBioChem 5 2004 214 223
53. E.B. De Oliveira, C. Humeau, E.R. Maia, L. Chebil, E. Ronat, G. Monard, M.F. Ruiz-Lopez, M. Ghoul, and J.-M. Engasser J. Mol. Catal. B: Enzym. 66 2010 325 331
54. M. Luić, Z. Stefanić, I. Ceilinger, M. Hodoscek, D. Janezic, T. Lenac, I.L. Asler, D. Sepac, and S. Tomić J. Phys. Chem. B 112 2008 4876 4883
55. I. Baum, B. Elsässer, L.W. Schwab, K. Loos, and G. Fels ACS Catal. 1 2011 323 336
56. P.B. Juhl, P. Trodler, S. Tyagi, and J. Pleiss BMC Struct. Biol. 9 2009 39
57. E. García-Urdiales, N. Ríos-Lombardía, J. Mangas-Sánchez, V. Gotor-Fernández, and V. Gotor Chembiochem 10 2009 1830 1838
58. C. Bidouil, E.B. De Oliveira, L. Chebil, E.R. Maia, B. Maigret, E. Ronat-Heidt, M. Ghoul, J.-M. Engasser, and C. Humeau J. Biotechnol. 156 2011 203 210
59. M.A.J. Veld, L. Fransson, A.R.A. Palmans, E.W. Meijer, and K. Hult ChemBioChem 10 2009 1330 1334
60. S. Raza, L. Fransson, and K. Hult Protein Sci. 10 2001 329 338
61. G. Fernandez-Lorente, Z. Cabrera, C. Godoy, R. Fernandez-Lafuente, J.M. Palomo, and J.M. Guisan Process Biochem. 43 2008 1061 1067
62. M.M. Bradford Anal. Biochem. 72 1976 248 254
63. A. Escorcia, J. Cruz, R. Torres, and C. Ortiz Vitae 18 2011 33 41
64. L. Gatterman Practices of Organic Chemistry, second ed 1961 159 162
65. C.S. Chen, S.H. Wu, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 109 1987 2812 2817
66. J. Uppenberg, M.T. Hansen, S. Patkar, and T.A. Jones Structure 2 1994 293 308
67. http://www.poissonboltzmann.org/pdb2pqr/.
68. T.J. Dolinsky, J.E. Nielsen, J.A. McCammon, and N.A. Baker Nucleic Acids Res. 32 2004 W665 W667
69. T.J. Dolinsky, P. Czodrowski, H. Li, J.E. Nielsen, J.H. Jensen, G. Klebe, and N.A. Baker Nucleic Acids Res. 35 2007 W522 W525
70. H. Li, A.D. Robertson, and J.H. Jensen Proteins: Struct. Funct. Bioinf. 61 2005 704 721
71. D.C. Bas, D.M. Rogers, and J.H. Jensen Proteins 73 2008 765 783
72. B.R. Brooks, C.L. Brooks, A.D. Mackerell, L. Nilsson, R.J. Petrella, B. Roux, Y. Won, G. Archontis, C. Bartels, S. Boresch, A. Caflisch, L. Caves, Q. Cui, A.R. Dinner, M. Feig, S. Fischer, J. Gao, M. Hodoscek, W. Im, K. Kuczera, T. Lazaridis, J. Ma, V. Ovchinnikov, E. Paci, R.W. Pastor, C.B. Post, J.Z. Pu, M. Schaefer, B. Tidor, R.M. Venable, H.L. Woodcock, X. Wu, W. Yang, D.M. York, and M. Karplus J. Comput. Chem. 30 2009 1545 1614
73. O. Trott, and A.J. Olson J. Comput. Chem. 31 2010 455 461
74. M.W. Chang, C. Ayeni, S. Breuer, and B.E. Torbett PLoS ONE 5 2010 e11955
75. A.M. Davis, and S.J. Teague Angew. Chem. 111 1999 778 792 Angew. Chem. Int. Ed. 38 (1999) 736-749
76. W. Humphrey, A. Dalke, and K. Schulten J. Mol. Graphics 14 1996 33 38
77. M.L. Testa, E. Zaballos, and R.J. Zaragozá Tetrahedron 68 2012 9583 9591
78. J.R. Satam, and R.V. Jayaram Catal. Commun. 9 2008 2365 2370
79. E.B. De Oliveira, C. Humeau, L. Chebil, E.R. Maia, F. Dehez, B. Maigret, M. Ghoul, and J.-M. Engasser J. Mol. Catal. B: Enzym. 59 2009 96 105
80. I. Vallikivi, L. Fransson, K. Hult, I. Järving, T. Pehk, N. Samel, V. Tõugu, L. Villo, and O. Parve J. Mol. Catal. B: Enzym. 35 2005 62 69
81. C. Palocci, M. Falconi, S. Alcaro, A. Tafi, R. Puglisi, F. Ortuso, M. Botta, L. Alberghina, and E. Cernia J. Biotechnol. 128 2007 908 918
82. H.B. Burgi, J.D. Dunitz, and E. Shefter J. Am. Chem. Soc. 95 1973 5065 5067