Enzymatic kinetic resolution of racemic ibuprofen: past, present and future

References

• Arroyo M, Sinisterra JV. (1994). High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: a mechanistic approach. J Org Chem, 59, 4410–17
   Web of Science ®Google Scholar
• Arroyo M, Moreno JM, Siniesterra JV. (1995). Alteration of the activity and selectivity of immobilized lipases by the effect of the amount of water in the organic medium. J Mol Cat A, 97, 195–201
   Web of Science ®Google Scholar
• Arroyo Sánchez M. (1995). Síntesis de ácidos 2-aril-propiónicos homoquirales mediante esterificación enantioselectiva catalizada por lipasas inmovilizadas. Thesis, Facultad de Farmacia, Universidad Complutense: Madrid
   Google Scholar
• Cárdenas F, de Castro MS, Sanchez-Montero JM, et al. (2001). Novel microbial lipases: catalytic activity in reactions in organic media. Enzyme Microb Technol, 28, 145–54
   PubMed Web of Science ®Google Scholar
• Ceynowa J, Rauchfleisz M. (2003). High enantioselective resolution of racemic 2-arylpropionic acids in an enzyme membrane reactor. J Mol Catal B, 23, 43–51
   Web of Science ®Google Scholar
• Chen J-C, Tsai S-W. (2000). Enantioselective synthesis of (S)-ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on Accurel MP1000. Biotechnol Progr, 16, 986–92
   PubMed Web of Science ®Google Scholar
• Contesini FJ, De Oliveira Carvalho P. (2006). Esterification of (RS)-ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids. Tetrahedron Asymmetry, 17, 2069–73
   Web of Science ®Google Scholar
• Dan-tong Z, Er-na X, Jia-xin W, et al. (2011). Enantioselective esterification of ibuprofen by a novel thermophilic biocatalyst: APE1547. Biotechnol Bioprocess Eng, 16, 638–44
   Web of Science ®Google Scholar
• De Oliveira Carvalho P, Cass QB, Calafatti SA, et al. (2006a). Review: alternatives for the separation of drug enantiomers: ibuprofen as a model compound. Braz J Chem Eng, 23, 291–300
   Web of Science ®Google Scholar
• De Oliveira Carvalho P, Contesini FJ, Bizaco R, et al. (2006b). Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger. J Ind Microbiol Biotechnol, 33, 713–18
   PubMed Web of Science ®Google Scholar
• De Oliveira Carvalho P, Contesini FJ, Ikegaki M. (2006c). Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources. Braz J Microbiol, 37, 329–337
   Web of Science ®Google Scholar
• Dominguez de María P, Maugeri Z. (2011). Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents. Curr Opin Chem Biol, 15, 220–5
   PubMed Web of Science ®Google Scholar
• Ducret A, Trani M, Pepin P, Lortie R. (1995). Comparison of two HPLC techniques for monitoring enantioselective reactions for the resolution of (R, S)-ibuprofen: chiral HPLC vs. achiral HPLC linked to an optical rotation detector. Biotechnol Tech, 9, 591–6
   Google Scholar
• Ducret A, Trani M, Lortie R. (1998). Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity. Enzyme Microb Technol, 22, 212–16
   Web of Science ®Google Scholar
• El-Feky HH, Cano-Òdena À, Gumí T. (2013). Facile synthesis of porous monolithic membrane microdevice. J Membr Sci, 439, 96–102
   Web of Science ®Google Scholar
• Ergan F, Trani M, Lortie R. (2006). Selective esterification of racemic ibuprofen. Ann N Y Acad Sci Enzyme Eng XII, 750, 228–31
   Google Scholar
• Evans AM. (2001). Comparative pharmacology of S(+)-Ibuprofen and (RS)-Ibuprofen. Clin Rheumatol, 20, S9–14
   PubMed Web of Science ®Google Scholar
• Foresti ML, Galle M, Ferreira ML, Briand LE. (2009). Enantioselective esterification of ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects. J Chem Technol Biotechnol, 84, 1461–73
   Web of Science ®Google Scholar
• Goldberg RJ. (2008). The Brown University Geriatric Psychopharmacology Update. Harvard News, 12(8), 1–5
   Google Scholar
• Hoobs HR, Thomas NR. (2007). Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev, 107, 2786–820
   PubMed Web of Science ®Google Scholar
• Hokenson MJ, Cope GA, Lewis ER, et al. (2000). Enzyme-induced strain/distortion in the ground-state ES complex in β-Lactamase catalysis revealed by FTIR. Biochemistry, 39, 6538–45
   PubMed Web of Science ®Google Scholar
• Hongwei Y, Jinchuan W, Chi Bun C. (2005). Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids. Chirality, 17, 16–21
   PubMed Web of Science ®Google Scholar
• Hudec R, Božeková L, Tisoňová J. (2012). Consumption of three most widely used analgesics in six European countries. J Clin Pharm Ther, 37, 78–80
   PubMed Web of Science ®Google Scholar
• Ikeda Y, Kurokawa Y. (2002). Enantioselective esterification of racemic ibuprofen in isooctane by immobilized lipase on cellulose acetate-titanium iso-propoxide gel fiber. J Biosci Bioeng, 93, 98–100
   PubMed Web of Science ®Google Scholar
• Iqbal A, Clifton IJ, Bagonis M, et al. (2009). Anatomy of a simple acyl intermediate in enzyme catalysis: combined biophysical and modeling studies on ornithine acetyl transferase. JACS, 131, 749
   PubMed Web of Science ®Google Scholar
• Itabaiana Jr, I, Soter de Mariz e Miranda L, Alves de Souza R. (2013). Towards a continuous flow environment for lipase-catalyzed reactions. J Mol Catal B, 1–9, 85–6
   Google Scholar
• José C, Briand LE. (2010). Deactivation of Novozym® 435 during the esterification of ibuprofen with ethanol: evidences of the detrimental effect of the alcohol. React Kinetics Mech Catal, 99, 17–22
   Web of Science ®Google Scholar
• José C, Bonetto RD, Gambaro LA, Guauque Torres MP, et al. (2011). Investigation of the causes of deactivation–degradation of the commercial biocatalyst Novozym® 435 in ethanol and ethanol–aqueous media. J Mol Catal B Enzymes, 71, 95–107
   Web of Science ®Google Scholar
• José C, Toledo MV, Osorio Grisales J, Briand LE. (2014). Effect of co-solvents in the enantioselective esterification of (R/S)-ibuprofen with ethanol. Curr Catal, 3, 131–8
   Google Scholar
• Klibanov AM. (1997). Why are enzymes less active in organic solvents than in water? Trends Biotechnol, 15, 97–101
   PubMed Web of Science ®Google Scholar
• Kim MG, Lee SB. (1996). Enzymatic resolution of racemic ibuprofen by lipase-catalyzed esterification reaction: effects of water content and solid supports. J Ferment Bioeng, 81, 269–71
   Google Scholar
• Kourist R, Domínguez de María P, Miyamoto K. (2011). Biocatalytic strategies for the asymmetric synthesis of profens – recent trends and developments. Green Chem, 13, 2607–18
   Web of Science ®Google Scholar
• Laane C, Boeren S, Voos K, Veeger C. (1987). Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng, 30, 81–7
   PubMed Web of Science ®Google Scholar
• Liu Y, Wang F, Tan T. (2009). Effects of alcohol and solvent on the performance of lipase from Candida sp. in enantioselective esterification of racemic ibuprofen. J Mol Catal B Enzymes, 56, 126–30
   Web of Science ®Google Scholar
• Long WS, Kamaruddin AH, Bhatia S. (2002). Enzymatic membrane reactor for chiral drugs synthesis. Jurnal Teknologi, 37, 27–44
   Google Scholar
• López N, Pérez R, Vázquez F, et al. (2002). Immobilisation of different Candida rugosa lipases by adsorption onto polypropylene powder: application to chiral synthesis of ibuprofen and trans-2-phenyl-1-cyclohexanol esters. J Chem Technol Biotechnol, 77, 175–82
   Web of Science ®Google Scholar
• López-Belmonte MT, Alcántara AR, Sinisterra JV. (1997). Enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized Rhizomucor miehei lipase. J Org Chem, 62, 1831–40
   Web of Science ®Google Scholar
• Lozano LJ, Godínez C, de los Ríos AP, et al. (2011). Recent advances in supported ionic liquid membrane technology. J Membr Sci, 376, 1–14
   Web of Science ®Google Scholar
• Marszałł MP, Siódmiak T. (2012). Immobilization of Candida rugosa lipase onto magnetic beads for kinetic resolution of (R, S)-ibuprofen. Catal Commun, 24, 80–4
   Web of Science ®Google Scholar
• Maugeri Z, Leitner W, Dominguez de Maria P. (2012). Practical separation of alcohol–ester mixtures using deep-eutectic-solvents. Tetrahedron Lett, 53, 6968–71
   Web of Science ®Google Scholar
• Miyako E, Maruyama T, Kamiya N, Goto, M. (2003). Enzyme-facilitated enantioselective transport of (S)-ibuprofen through a supported liquid membrane based on ionic liquids. Chem Commun, 7, 2926–7
   Google Scholar
• Overmeyer A, Schrader-Lippelt S, Kasche V, Brunner G. (1999). Lipase-catalysed kinetic resolution of racemates at temperatures from 40 °C to 160 °C in supercritical CO2. Biotechnol Lett, 21, 65–9
   Web of Science ®Google Scholar
• Pepin R, Lortie R. (1999). Influence of water activity on the enantioselective esterification of (R, S)-ibuprofen by Candida antarctica lipase B in solventless media. Biotechnol Bioeng, 63, 502–5
   PubMed Web of Science ®Google Scholar
• Persson M, Costes D, Wehtje E, Adlercreutz P. (2002). Effects of solvent, water activity and temperature on lipase and hydroxynitrile lyase enantioselectivity. Enzyme Microb Technol, 30, 916–23
   Web of Science ®Google Scholar
• Phleps W. (2001). Overview on clinical data of Dexibuprofen. Clin Rheumatol, 20, S15–21
   PubMed Web of Science ®Google Scholar
• Rantakylä M, Aaltonen O. (1994). Enantioselective esterification of ibuprofen in supercritical carbon dioxide by immobilized lipase. Biotechnol Lett, 16, 825–30
   Web of Science ®Google Scholar
• Ríos GM, Belleville MP, Paolucci D, Sanchez J. (2004). Progress in enzymatic membrane reactor – a review. J Membr Sci, 242, 189–96
   Web of Science ®Google Scholar
• Sánchez A, Valero F, Lafuente J, Solá C. (2000). Highly enantioselective esterification of racemic ibuprofen in a packed bed reactor using immobilized Rhizomucor miehei lipase. Enzyme Microb Technol, 27, 157–66
   PubMed Web of Science ®Google Scholar
• Toledo MV, José C, Collins SE, et al. (2012). Esterification of R/S-ketoprofen with 2-propanol as reactant and solvent catalyzed by Novozym® 435 at selected conditions. J Mol Catal B, 83, 108–19
   Web of Science ®Google Scholar
• Trani M, Ducret A, Pepin P, Lortie R. (1995). Scale up of the enantioselective reaction for the enzymatic resolution of (R, S)-ibuprofen. Biotechnol Lett, 17, 1095–8
   Web of Science ®Google Scholar
• Won K, Hong J-K, Jim K-J, Moon S-J. (2006). Lipase-catalyzed enantioselective esterification of racemic ibuprofen coupled with pervaporation. Process Biochem, 41, 264–9
   Web of Science ®Google Scholar
• Xie Y-C, Liu H-Z, Chen J-Y. (1998). Candida rugosa lipase catalyzed esterification of racemic ibuprofen with butanol: racemization of R-ibuprofen and chemical hydrolysis of S-ester formed. Biotechnol Lett, 20, 455–8
   Web of Science ®Google Scholar