Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study
The chemo- and enantioselectivity of the Candida antarctica lipase B (CalB)-catalyzed acetylation reaction of (R,S)-propranolol using vinyl acetate as acyl donor and toluene as organic solvent was studied. Because of the poor solubility of propranolol in toluene small quantities of methanol were add...
Published in: | Journal of Molecular Catalysis B: Enzymatic |
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ftunisantotomasc:oai:repository.usta.edu.co:11634/21014 2024-09-15T17:48:23+00:00 Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study Escorcia, Andrés M. Molina, Daniel Daza, Martha C. Doerr, Markus CRAI-USTA Bogotá 2013-09-25 application/pdf http://hdl.handle.net/11634/21014 https://doi.org/10.1016/j.molcatb.2013.09.019 unknown A.M. Barret, J. Pharmacol. 16 (1985) 95–108 R. Rabkin, D.P. Stables, N.W. Levin, M.M. Suzman, Am. J. Cardiol. 18 (1966) 370–380. E.M. Besterman, D.H. Friedlander, Postgrad. Med. J. 41 (1965) 526–535. C.V.S. Ram, Am. J. Cardiol. 102 (2008) 242–244. S. Belknap, Evid. Based. Med. 13 (2008) 50. D. Patakas, V. Argiropoulou, G. Louridas, V. Tsara, Thorax 38 (1983) 108–112. H.S. Bevinakatti, A.A. Banerji, J. Org. Chem. 56 (1991) 5372–5375. S.V. Darnle, P.N. Patil, M.M. Salunkhe, Synth. Commun. 29 (1999) 3855–3862. A. Kamal, M. Sandbhor, A. Ali Shaik, Bioorg. Med. Chem. Lett. 14 (2004) 4581–4583. R.A. Veloo, G.-J. Koomen, Tetrahedron: Asymmetry 4 (1993) 2401–2404. H. Sasai, N. Itoh, T. Suzuki, M. Shibasaki, Tetrahedron Lett. 34 (1993) 855–858. Y.-F. Wang, S.-T. Chen, K.K.-C. Liu, C.-H. Wong, Tetrahedron Lett. 30 (1989) 1917–1920. O. Barbosa, C. Ariza, C. Ortiz, R. Torres, New Biotechnol. 27 (2010) 844–850. T.-W. Chiou, C.-C. Chang, C.-T. Lai, D.-F. Tai, Bioorg. Med. Chem. Lett. 7 (1997) 433–436. R. Ávila-González, M. Pérez-Gilabert, F. García-Carmona, J. Biosci. Bioeng. 100 (2005) 423–428. R. Ávila, R. Ruiz, D. Amaro-González, O. Díaz, J.A. González, A.J. Núnez, ˜ Lat. Am. Appl. Res. 35 (2005) 307–311. V. Gotor-Fernández, R. Brieva, V. Gotor, J. Mol. Catal. B: Enzym. 40 (2006) 111–120. A. Ghanem, H.Y. Aboul-Enein, Tetrahedron: Asymmetry 15 (2004) 3331–3351. A. Ghanem, Tetrahedron 63 (2007) 1721–1754. M.T. Reetz, Curr. Opin. Chem. Biol. 6 (2002) 145–150. http://hdl.handle.net/11634/21014 https://doi.org/10.1016/j.molcatb.2013.09.019 Atribución-NoComercial-CompartirIgual 2.5 Colombia http://creativecommons.org/licenses/by-nc-sa/2.5/co/ Candida antarctica lipase B Chiral resolution Molecular modeling NMR spectroscopy Chemoselectivity Generación de Nuevo Conocimiento: Artículos publicados en revistas especializadas - Electrónicos 2013 ftunisantotomasc https://doi.org/10.1016/j.molcatb.2013.09.019 2024-06-25T03:49:39Z The chemo- and enantioselectivity of the Candida antarctica lipase B (CalB)-catalyzed acetylation reaction of (R,S)-propranolol using vinyl acetate as acyl donor and toluene as organic solvent was studied. Because of the poor solubility of propranolol in toluene small quantities of methanol were added as cosolvent. The effects of the propranolol/vinyl acetate ratio, the enzyme purification procedure and the methanol concentration on the reaction were investigated. The reactions occurring in the system were quantitatively investigated using 1H and 13C NMR spectroscopy. The major reactions were the hydrolysis and alcoholysis of vinyl acetate, as a consequence of the presence of residual water and methanol in the reaction medium. Furthermore, the NMR analysis confirmed that O-acetyl-propranolol was formed exclusively. The reaction was also found to be enantioselective favoring the faster transformation of the R-propranolol. In addition to the experiments, molecular modeling was used to study the formation of the reactive Michaelis complexes between propranolol and acetylated CalB, using a combined molecular docking and molecular dynamics (MD) procedure. Only for the O-acetylation we found binding modes of the substrate leading to formation of the product, which explains the experimentally observed chemoselectivity of CalB. http://unidadinvestigacion.usta.edu.co Other/Unknown Material Antarc* Antarctica Repositorio Institucional de la Universidad Santo Tomás Journal of Molecular Catalysis B: Enzymatic 98 21 29 |
institution |
Open Polar |
collection |
Repositorio Institucional de la Universidad Santo Tomás |
op_collection_id |
ftunisantotomasc |
language |
unknown |
topic |
Candida antarctica lipase B Chiral resolution Molecular modeling NMR spectroscopy Chemoselectivity |
spellingShingle |
Candida antarctica lipase B Chiral resolution Molecular modeling NMR spectroscopy Chemoselectivity Escorcia, Andrés M. Molina, Daniel Daza, Martha C. Doerr, Markus Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
topic_facet |
Candida antarctica lipase B Chiral resolution Molecular modeling NMR spectroscopy Chemoselectivity |
description |
The chemo- and enantioselectivity of the Candida antarctica lipase B (CalB)-catalyzed acetylation reaction of (R,S)-propranolol using vinyl acetate as acyl donor and toluene as organic solvent was studied. Because of the poor solubility of propranolol in toluene small quantities of methanol were added as cosolvent. The effects of the propranolol/vinyl acetate ratio, the enzyme purification procedure and the methanol concentration on the reaction were investigated. The reactions occurring in the system were quantitatively investigated using 1H and 13C NMR spectroscopy. The major reactions were the hydrolysis and alcoholysis of vinyl acetate, as a consequence of the presence of residual water and methanol in the reaction medium. Furthermore, the NMR analysis confirmed that O-acetyl-propranolol was formed exclusively. The reaction was also found to be enantioselective favoring the faster transformation of the R-propranolol. In addition to the experiments, molecular modeling was used to study the formation of the reactive Michaelis complexes between propranolol and acetylated CalB, using a combined molecular docking and molecular dynamics (MD) procedure. Only for the O-acetylation we found binding modes of the substrate leading to formation of the product, which explains the experimentally observed chemoselectivity of CalB. http://unidadinvestigacion.usta.edu.co |
format |
Other/Unknown Material |
author |
Escorcia, Andrés M. Molina, Daniel Daza, Martha C. Doerr, Markus |
author_facet |
Escorcia, Andrés M. Molina, Daniel Daza, Martha C. Doerr, Markus |
author_sort |
Escorcia, Andrés M. |
title |
Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
title_short |
Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
title_full |
Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
title_fullStr |
Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
title_full_unstemmed |
Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study |
title_sort |
acetylation of (r,s)-propranolol catalyzed by candida antarctica lipase b: an experimental and computational study |
publishDate |
2013 |
url |
http://hdl.handle.net/11634/21014 https://doi.org/10.1016/j.molcatb.2013.09.019 |
op_coverage |
CRAI-USTA Bogotá |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
A.M. Barret, J. Pharmacol. 16 (1985) 95–108 R. Rabkin, D.P. Stables, N.W. Levin, M.M. Suzman, Am. J. Cardiol. 18 (1966) 370–380. E.M. Besterman, D.H. Friedlander, Postgrad. Med. J. 41 (1965) 526–535. C.V.S. Ram, Am. J. Cardiol. 102 (2008) 242–244. S. Belknap, Evid. Based. Med. 13 (2008) 50. D. Patakas, V. Argiropoulou, G. Louridas, V. Tsara, Thorax 38 (1983) 108–112. H.S. Bevinakatti, A.A. Banerji, J. Org. Chem. 56 (1991) 5372–5375. S.V. Darnle, P.N. Patil, M.M. Salunkhe, Synth. Commun. 29 (1999) 3855–3862. A. Kamal, M. Sandbhor, A. Ali Shaik, Bioorg. Med. Chem. Lett. 14 (2004) 4581–4583. R.A. Veloo, G.-J. Koomen, Tetrahedron: Asymmetry 4 (1993) 2401–2404. H. Sasai, N. Itoh, T. Suzuki, M. Shibasaki, Tetrahedron Lett. 34 (1993) 855–858. Y.-F. Wang, S.-T. Chen, K.K.-C. Liu, C.-H. Wong, Tetrahedron Lett. 30 (1989) 1917–1920. O. Barbosa, C. Ariza, C. Ortiz, R. Torres, New Biotechnol. 27 (2010) 844–850. T.-W. Chiou, C.-C. Chang, C.-T. Lai, D.-F. Tai, Bioorg. Med. Chem. Lett. 7 (1997) 433–436. R. Ávila-González, M. Pérez-Gilabert, F. García-Carmona, J. Biosci. Bioeng. 100 (2005) 423–428. R. Ávila, R. Ruiz, D. Amaro-González, O. Díaz, J.A. González, A.J. Núnez, ˜ Lat. Am. Appl. Res. 35 (2005) 307–311. V. Gotor-Fernández, R. Brieva, V. Gotor, J. Mol. Catal. B: Enzym. 40 (2006) 111–120. A. Ghanem, H.Y. Aboul-Enein, Tetrahedron: Asymmetry 15 (2004) 3331–3351. A. Ghanem, Tetrahedron 63 (2007) 1721–1754. M.T. Reetz, Curr. Opin. Chem. Biol. 6 (2002) 145–150. http://hdl.handle.net/11634/21014 https://doi.org/10.1016/j.molcatb.2013.09.019 |
op_rights |
Atribución-NoComercial-CompartirIgual 2.5 Colombia http://creativecommons.org/licenses/by-nc-sa/2.5/co/ |
op_doi |
https://doi.org/10.1016/j.molcatb.2013.09.019 |
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Journal of Molecular Catalysis B: Enzymatic |
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98 |
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21 |
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29 |
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