Silica-immobilized enzyme reactors

Journal of Liquid Chromatography and Related Technologies

Volumn 31, Issue 11-12, 2008, Pages 1568-1592

  Luckarift, Heather R ^a  

^a AIR FORCE RESEARCH LABORATORY   (United States)

Author keywords

Biocatalysis; Biosilica; Drug discovery; Enzyme reactors; IMER; Immobilized enzymes

Indexed keywords

ENZYME IMMOBILIZATION; FOOD ADDITIVES; MATRIX ALGEBRA; SILICA; SILICATE MINERALS; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL);

BIOCHEMICAL SYNTHESIS; CARRIER MATRIX; ENZYMATIC PROPERTIES; FLOW THROUGH; IMMOBILIZATION TECHNIQUES; IMMOBILIZED ENZYME REACTOR (IMER); MODEL SYSTEMS; REPRODUCIBILITY; SILICA MATRICES;

ENZYMES;

5 (1 AZIRIDINYL) 2,4 DINITROBENZAMIDE; 6 AMINOPENICILLANIC ACID; ACETYLCHOLINESTERASE; ACETYLSALICYLIC ACID; ADRENALIN; AROMATIC NITRO COMPOUND; BETA GLUCURONIDASE; BETA LACTAM ANTIBIOTIC; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; DEXTROMETHORPHAN; DEXTRORPHAN; DOPAMINE; DOPAMINE BETA MONOOXYGENASE; DRUG METABOLITE; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; HYMECROMONE; IBUPROFEN; NITROBENZENE; NITROFURAL; NORADRENALIN; NORMETADRENALIN; PARACETAMOL; PENICILLIN AMIDASE; PHENYLETHANOLAMINE N METHYLTRANSFERASE; POLYETHYLENEIMINE; PRODRUG; SILICON DIOXIDE; TRIACYLGLYCEROL LIPASE; UNINDEXED DRUG;

ARTIFICIAL MEMBRANE; BINDING AFFINITY; BIOCATALYST; BIOENGINEERING; BIOREACTOR; BIOSENSOR; CANDIDA RUGOSA; CAPILLARY ELECTROCHROMATOGRAPHY; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG SCREENING; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME IMMOBILIZATION; ENZYME INHIBITION; ENZYME KINETICS; FLOW KINETICS; FLOW RATE; GLUCURONIDATION; HUMAN; HYDROLYSIS; IMMOBILIZED ENZYME REACTOR; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; MICHAELIS MENTEN KINETICS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NONHUMAN; PROTEIN ANALYSIS; PROTEIN DETERMINATION; PROTEIN FUNCTION; REPRODUCIBILITY; REVIEW;

EID: 45849096088     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070802125959     Document Type: Review

References (116)

1. Liang, J.F.; Li, Y.T.; Yang, V.C. Biomedical application of immobilized enzymes. J. Pharm. Sci. 2000, 89, 979-990.
2. Cao, L. Immobilised enzymes: science or art? Curr. Opin. Chem. Biol. 2005, 9, 217-226.
3. Katchalski-Katzir, E. Immobilized enzymes-learning from past successes and failures. Trends Biotechnol. 1993, 11, 471-478.
4. Bornscheuer, U.T. Immobilizing enzymes: how to create more suitable biocatalysts. Angew. Chem. Int. Ed. 2003, 42, 3336-3337.
5. Sheldon, R. Enzyme Immobilization: the Quest for Optimum Preformance. Adv. Synth. Catal. 2007, 349, 1289-1307.
6. Krenkova, J.; Bilkova, Z.; Foret, F. Characterization of a monolithic immobilized trypsin microreactor with on-line coupling to ESI-MS. J. Sep. Sci. 2005, 28, 1675-1684.
7. Temporini, C.; Perani, E.; Mancini, F.; Bartolini, M.; Calleri, E.; Lubda, D.; Felix, G.; Andrisano, V.; Massolini, G. Optimization of a trypsin-bioreactor coupled with high-performance liquid chromatography- electrospray ionization tandem mass spectrometry for quality control of biotechnological drugs. J. Chromatogr. A 2006, 1120, 121-131.
8. Urban, P.L.; Goodall, D.M.; Bruce, N.C. Enzymatic microreactors in chemical analysis and kinetic studies. Biotechnol. Adv. 2006, 24, 42-57.
9. Massolini, G.; Calleri, E. Immobilized trypsin systems coupled on-line to separation methods: recent developments and analytical applications. J. Sep. Sci. 2005, 28, 7-21.
10. Kato, M.; Inuzuka, K.; Sakai-Kato, K.; Toyo'oka, T. Monolithic bioreactor immobilizing trypsin for high-throughput analysis. Anal. Chem. 2005, 77, 1813-1818.
11. Mateo, C.; Palomo, J.M.; Fernandez-Lorente, G.; Guisan, J.M.; Fernandez-Lafuente, R. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microbial Technol. 2007, 40, 1451-1463.
12. Mozahev, V.V.; Melik-Nubarov, N.S.; Sergeeva, M.V.; Sikrnis, V.; Martinek, K. Strategy for stabilizing enzymes. I. Increasing stability of enzymes via their multipoint interaction with a support. Biocatalysis 1990, 3, 179-187.
13. Klibanov, A.M. Stabilization of enzymes against thermal inactivation. Adv. App. Micro. 1983, 29, 1-28.
14. Palomo, J.M.; Fernandez-Lorente, G.; Mateo, C.; Ortiz, C.; Fernandez-Lafuente, R.; Guisan, J.M. Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters. Enzyme Microbial Technol. 2002, 31, 775-783.
15. Fernandez-Lafuente, R.; Armisen, P.; Sabuquillo, P.; Fernandez-Lorente, G.; Guisan, M. J. Immobilization of lipases by selective adsorption on hydrophobic supports. Chem. Phys. Lipids 1998, 93, 185-197.
16. Petkar, M.; Lali, A.; Caimi, P.; Daminati, M. Immobilization of lipases for non-aqueous synthesis. J. Mol. Catal. B: Enzymatic 2006, 39, 83-90.
17. Avnir, D.; Lev, O.; Livage, J. Recent bio-applications of sol-gel materials. J. Mat. Chem. 2006, 16, 1013-1030.
18. Gill, I.; Ballesteros, A. Bioencapsulation within synthetic polymers (Part 1): sol-gel encapsulated biologicals. Trends Biotechnol. 2000, 18, 282-296.
19. Besanger, T.R.; Hodgson, R.J.; Green, J.R.A.; Brennan, J.D. Immobilized enzyme reactor chromatography: optimization of protein retention and enzyme activity in monolithic silica stationary phases. Anal. Chim. Acta 2006, 564, 106-115.
20. Shimizu, K.; Cha, J.; Stucky, G.D.; Morse, D.E. Silicatein alpha: cathepsin L-like protein in sponge biosilica. Proc. Nat. Acad. Sci. 1998, 95, 6234-6238.
21. Cha, J.N.; Shimizu, K.; Zhou, Y.; Christiansen, S.C.; Chmelka, B.F.; Stucky, G.D.; Morse, D.E. Silicatein filaments and subunits from a marine sponge direct the polymerization of silica and silicones in vitro. Proc. Nat. Acad. Sci. 1999, 96, 361-365.
22. Kroger, N.; Deutzmann, R.; Sumper, M. Polycationic peptides from diatom biosilica that direct silica nanosphere formation. Science 1999, 286, 1129-1132.
23. Luckarift, H.R.; Spain, J.C.; Naik, R.R.; Stone, M.O. Enzyme immobilization in a biomimetic silica support. Nat. Biotechnol. 2004, 22, 211-213.
24. Naik, R.R.; Tomczak, M.M.; Luckarift, H.R.; Spain, J.C.; Stone, M.O. Entrapment of enzymes and nanoparticles using biomimetically synthesized silica. Chem. Commun. (Camb) 2004, 1684-1685.
25. Burns, K.L.; May, S.W. Separation methods applicable to the evaluation of enzyme-inhibitor and enzyme-substrate interactions. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2003, 797, 175-190.
26. Emneus, J.; Marko-Varga, G. Biospecific detection in liquid chromatography. J. Chromatogr. A. 1995, 703, 191-243.
27. Ono, M.; Idei, N.; Nakajima, T.; Itoh, Y.; Kawakami, N.; Shimada, K.; Yamato, S. Simultaneous determination of riboflavin phosphate and other ingredients in a multivitamin pharmaceutical preparation by on-line automated LC coupled with pre-column immobilized enzyme reactor. J. Pharm. Biomed. Anal. 2002, 29, 325-334.
28. Yamato, S.; Kawakami, N.; Shimada, K.; Ono, M.; Idei, N.; Itoh, Y. On-line automated high-performance liquid chromatographic determination of total riboflavin phosphates using immobilized acid phosphatase as a precolumn reactor. J. Chromatogr. A 2000, 896, 171-181.
29. Wada, M.; Inoue, K.; Thara, A.; Kishikawa, N.; Nakashima, K.; Kuroda, N. Determination of organic peroxides by liquid chromatography with on-line post-column ultraviolet irradiation and peroxyoxalate chemiluminescence detection. J. Chromatogr. A 2003, 987, 189-195.
30. Marko-Varga, G.; Dominguez, E.; Hahn-Hagerdal, B.; Gorton, L. Bioselective detection in liquid chromatography by the use of immobilized enzymes. J. Pharm. Biomed. Anal. 1990, 8, 817-823.
31. Jansen, H.; Brinkman, U.A.; Frei, R.W. Stereoselective determination of L-amino acids using column liquid chromatography with an enzymatic solid-phase reactor and chemiluminescence detection. J. Chromatogr. 1988, 440, 217-223.
32. Werkhoven-Goewie, C.E.; de Ruiter, C.; Brinkman, U.A.; Frei, R.W.; de Jong, G.J.; Little, C.J.; Stahel, O. Automated determination of drugs in blood samples after enzymatic hydrolysis using precolumn switching and post-column reaction detection. J. Chromatogr. 1983, 255, 79-90.
33. Girelli, A.M.; Mattei, E. Application of immobilized enzyme reactor in on-line high performance liquid chromatography: a review. J. Chromatogr. B. Anal. Technol. Biomed. Life Sci. 2005, 819, 3-16.
34. Kerby, M.B.; Legge, R.S.; Tripathi, A. Measurements of kinetic parameters in a microfluidic reactor. Anal. Chem. 2006, 78, 8273-8280.
35. Luckarift, H.R.; Johnson, G.R.; Spain, J.C. Silica-immobilized enzyme reactors; application to cholinesterase-inhibition studies. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2006, 843, 310-316.
36. Andrisano, V.; Bartolini, M.; Gotti, R.; Cavrini, V.; Felix, G. Determination of inhibitors' potency (IC50) by a direct high-performance liquid chromatographic method on an immobilised acetylcholinesterase column. J. Chromatogr. B. Biomed. Sci. Appl. 2001, 753, 375-383.
37. Jadaud, P.; Wainer, I.W. The stereochemical resolution of the enantiomers of aspartame on an immobilized alpha-chymotrypsin HPLC chiral stationary phase: the effect of mobile-phase composition and enzyme activity. Chirality 1990, 2, 32-37.
38. Gottschalk, I.; Lagerquist, C.; Zuo, S.S.; Lundqvist, A.; Lundahl, P. Immobilized-biomembrane affinity chromatography for binding studies of membrane proteins. J. Chromatogr. B. Anal. Technol. Biomed. Life Sci. 2002, 768, 31-40.
39. Lundqvist, A.; Lundahl, P. Advantages of quantitative affinity chromatography for the analysis of solute interaction with membrane proteins. J. Biochem. Biophys. Meth. 2001, 49, 507-521.
40. Moaddel, R.; Lu, L.; Baynham, M.; Wainer, I.W. Immobilized receptorand transporter-based liquid chromatographic phases for on-line pharmacological and biochemical studies: a mini-review. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002, 768, 41-53.
41. Bertucci, C.; Bartolini, M.; Gotti, R.; Andrisano, V. Drug affinity to immobilized target bio-polymers by high-performance liquid chromatography and capillary electrophoresis. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2003, 797, 111-129.
42. Kawakami, K.; Sera, Y.; Sakai, S.; Ono, T.; Ijima, H. Development and characterization of a silica monolith immobilized enzyme micro-bioreactor. Ind. Eng. Chem. Res. 2005, 44, 236-240.
43. Josic, D.; Buchacher, A. Application of monoliths as supports for affinity chromatography and fast enzymatic conversion. J. Biochem. Biophys. Methods 2001, 49, 153-174.
44. Calleri, E.; Massolini, G.; Lubda, D.; Temporini, C.; Loiodice, F.C.; Caccialanza, G. Evaluation of a monolithic epoxy silica support for penicillin G acylase immobilization. J. Chromatogr. A 2004, 1031, 93-100.
45. Ostryanina, N.D.; Vlasov, G.P.; Tennikova, T.B. Multifunctional fractionation of polyclonal antibodies by immunoaffinity high-performance monolithic disk chromatography. J. Chromatogr. A 2002, 949, 163-171.
46. Liu, H.; Carter, G.T.; Tischler, M. Immobilized artificial membrane chromatography with mass spectrometric detection: a rapid method for screening drug-membrane interactions. Rapid Comm. Mass Spec. 2001, 15, 1533-1538.
47. Krause, E.; Dathe, M.; Wieprecht, T.; Bienert, M. Noncovalent immobilized artificial membrane chromatography, an improved method for describing peptide-lipid bilayer interactions. J. Chromatogr. A 1999, 849, 125-133.
48. Luco, J.M.; Salinas, A.P.; Torriero, A.A.; Vazquez, R.N.; Raba, J.; Marchevsky, E. Immobilized artificial membrane chromatography: quantitative structure-retention relationships of structurally diverse drugs. J. Chem. Info. Computer Sci. 2003, 43, 2129-2136.
49. Masucci, J.A.; Caldwell, G.W.; Foley, J.P. Comparison of the retention behavior of beta-blockers using immobilized artificial membrane chromatography and lysophospholipid micellar electrokinetic chromatography. J. Chromatogr. A 1998, 810, 95-103.
50. Pehourcq, F.; Jarry, C.; Bannwarth, B. Potential of immobilized artificial membrane chromatography for lipophilicity determination of arylpropionic acid non-steroidal anti-inflammatory drugs. J. Pharm. Biomed. Anal. 2003, 33, 137-144.
51. Pidgeon, C.; Stevens, J.; Otto, S.; Jefcoate, C.; Marcus, C. Immobilized artificial membrane chromatography: rapid purification of functional membrane proteins. Anal. Biochem. 1991, 194, 163-173.
52. Pidgeon, C.; Venkataram, U.V. Immobilized artificial membrane chromatography: supports composed of membrane lipids. Anal. Biochem. 1989, 176, 36-47.
53. Stewart, B.H.; Chan, O.H. Use of immobilized artificial membrane chromatography for drug transport applications. J. Pharm. Sci. 1998, 87, 1471-1478.
54. Yang, C.Y.; Cai, S.J.; Liu, H.; Pidgeon, C. Immobilized artificial membranes-screens for drug membrane interactions. Adv. Drug Delivery Rev. 1996, 23, 229-256.
55. Cloix, J.F.; Wainer, I.W. Development of an immobilized brain glutamine synthetase liquid chromatographic stationary phase for on-line biochemical studies. J. Chromatogr. A. 2001, 913, 133-140.
56. Luckarift, H.R.; Nadeau, L.J.; Spain, J.C. Continuous synthesis of aminophenols from nitroaromatic compounds by combination of metal and biocatalyst. Chem. Commun. (Camb) 2005, 383-384.
57. Luckarift, H.R.; Balasubramanian, S.; Paliwal, S.; Johnson, G.R.; Simonian, A.L. Enzyme-encapsulated silica monolayers for rapid functionalization of a gold surface. Coll. Surf. B Biointerfaces 2007, 58, 28-33.
58. Luckarift, H.; Ku, B.; Dordick, J.; Spain, J. Silica-Immobilized Enzymes for multi-step synthesis in microfluidic devices. Biotech. Bioeng. 2007, 98, 701-705.
59. Luckarift, H.; Greenwald, R.; Bergin, M.; Spain, J.; Johnson, G. Biosensor system for continuous monitoring of organophosphate aerosols. Biosens. Bioelectron. 2007, 23, 400-406.
60. Yao, L.X.; Wu, Z.C.; Ji, Z.L.; Chen, Y.Z.; Chen, X. Internet resources related to drug action and human response: a review. Appl. Bioinformatics 2006, 5, 131-139.
61. Dannhardt, G.; Kiefer, W. Cyclooxygenase inhibitors-current status and future prospects. Eur. J. Med. Chem. 2001, 36, 109-126.
62. Asberg, M.; Eriksson, B.; Martensson, B.; Traskman-Bendz, L.; Wagner, A. Therapeutic effects of serotonin uptake inhibitors in depression. J. Clin. Psychiat. 1986, 47 Suppl, 23-35.
63. Lemberger, L.; Fuller, R.W.; Zerbe, R.L. Use of specific serotonin uptake inhibitors as antidepressants. Clin. Neuropharmacol. 1985, 8, 299-317.
64. Youdim, M.B.; Edmondson, D.; Tipton, K.F. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci. 2006, 7, 295-309.
65. Liston, D.R.; Nielsen, J.A.; Villalobos, A.; Chapin, D.; Jones, S.B.; Hubbard, S.T.; Shalaby, I.A.; Ramirez, A.; Nason, D.; White, W.F. Pharmacology of selective acetylcholinesterase inhibitors: implications for use in Alzheimer's disease. Eur. J. Pharmacol. 2004, 486, 9-17.
66. Holden, M.; Kelly, C. Use of cholinesterase inhibitors in dementia. Adv. Psychiat. Treat. 2002, 8, 89-96.
67. Darvesh, S.; Walsh, R.; Kumar, R.; Caines, A.; Roberts, S.; Magee, D.; Rockwood, K.; Martin, E. Inhibition of human cholinesterases by drugs used to treat Alzheimer disease. Alzheimer Dis. Assoc. Disord. 2003, 17, 117-126.
68. Giacobini, E. Cholinesterase inhibitors: new roles and therapeutic alternatives. Pharmacol. Res. 2004, 50, 433-440.
69. Birks, J. Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst. Rev. 2006, CD005593.
70. Hitzeman, N. Cholinesterase inhibitors for Alzheimer's disease. Am. Fam. Physician 2006, 74, 747-749.
71. Bajgar, J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Adv. Clin. Chem. 2004, 38, 151-216.
72. Wiener, S.W.; Hoffman, R.S. Nerve agents: a comprehensive review. J Intensive Care Med. 2004, 19, 22-37.
73. Bartolini, M.; Cavrini, V.; Andrisano, V. Choosing the right chromatographic support in making a new acetylcholinesterase-micro-immobilised enzyme reactor for drug discovery. J. Chromatogr. A 2005, 1065, 135-144.
74. Bartolini, M.; Cavrini, V.; Andrisano, V. Monolithic micro- immobilizedenzyme reactor with human recombinant acetylcholinesterase for on-line inhibition studies. J. Chromatogr. A 2004, 1031, 27-34.
75. Suwansa-ard, S.; Kanatharana, P.; Asawatreratanakul, P.; Limsakul, C.; Wongkittisuksa, B.; Thavarungkul, P. Semi disposable reactor biosensors for detecting carbamate pesticides in water. Biosens. Bioelectron. 2005, 21, 445-454.
76. Dong, Y.; Wang, L.; Shangguan, D.; Zhao, R.; Liu, G. Improved method for the routine determination of acetylcholine and choline in brain microdialysate using a horseradish peroxidase column as the immobilized enzyme reactor. J. Chromatogr. B. Anal. Technol. Biomed. Life Sci. 2003, 788, 193-198.
77. Kim, H.S.; Wainer, I.W. The covalent immobilization of microsomal uridine diphospho-glucuronosyltransferase (UDPGT): initial synthesis and characterization of an UDPGT immobilized enzyme reactor for the on-line study of glucuronidation. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2005, 823, 158-166.
78. Sakai-Kato, K.; Kato, M.; Toyo'oka, T. On-line drug-metabolism system using microsomes encapsulated in a capillary by the sol-gel method and integrated into capillary electrophoresis. Anal. Biochem. 2002, 308, 278-284.
79. Calleri, E.; Marrubini, G.; Massolini, G.; Lubda, D.; de Fazio, S.S.; Furlanetto, S.; Wainer, I.W.; Manzo, L.; Caccialanza, G. Development of a chromatographic bioreactor based on immobilized beta-glucuronidase on monolithic support for the determination of dextromethorphan and dextrorphan in human urine. J. Pharm. Biomed. Anal. 2004, 35, 1179-1189.
80. Tsunoda, M. Recent advances in methods for the analysis of catecholamines and their metabolites. Anal. Bioanal. Chem. 2006, 386, 506-514.
81. Markoglou, N.; Wainer, I.W. Biosynthesis in an on-line immobilizedenzyme reactor containing phenylethanolamine N-methyltransferase in single-enzyme and coupled-enzyme formats. J. Chromatogr. A 2002, 948, 249-256.
82. Markoglou, N.; Wainer, I.W. Synthesis and characterization of immobilized dopamine beta-hydroxylase in membrane-bound and solubilized formats. J. Biochem. Biophys. Meth. 2001, 48, 61-75.
83. Markoglou, N.; Wainer, I.W. Synthesis and characterization of an immobilized phenylethanolamine N-methyltransferase liquid chromatographic stationary phase. Anal. Biochem. 2001, 288, 83-88.
84. Markoglou, N.; Hsuesh, R.; Wainer, I.W. Immobilized enzyme reactors based upon the flavoenzymes monoamine oxidase A and B. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2004, 804, 295-302.
85. Markoglou, N.; Wainer, I.W. On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002, 766, 145-151.
86. Goto, Y.; Grace, A.A. The Dopamine System and the Pathophysiology of Schizophrenia: a Basic Science Perspective. Int. Rev. Neurobiol. 2007, 78C, 41-68.
87. Berne, C.; Betancor, L.; Luckarift, H.R.; Spain, J.C. Application of a microfluidic reactor for screening cancer prodrug activation using silica-immobilized nitrobenzene nitroreductase. Biomacromol. 2006, 7, 2631-2636.
88. Opperdoes, F.R. Topogenesis of glycolytic enzymes in Trypanosoma brucei. Biochem. Soc. Symp. 1987, 53, 123-129.
89. Bartolini, M.; Andrisano, V.; Wainer, I.W. Development and characterization of an immobilized enzyme reactor based on glyceraldehyde-3- phosphate dehydrogenase for on-line enzymatic studies. J. Chromatogr. A 2003, 987, 331-340.
90. Straathof, A.J.; Panke, S.; Schmid, A. The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol. 2002, 13, 548-556.
91. Bhat, M.K. Cellulases and related enzymes in biotechnology. Biotechnol. Adv. 2000, 18, 355-383.
92. Panke, S.; Held, M.; Wubbolts, M. Trends and innovations in industrial biocatalysis for the production of fine chemicals. Curr. Opin. Biotechnol. 2004, 15, 272-279.
93. Michels, P.C.; Khmelnitsky, Y.L.; Dordick, J.S.; Clark, D.S. Combinatorial biocatalysis: a natural approach to drug discovery. Trends Biotechnol. 1998, 16, 210-215.
94. Faber, K.; Franssen, M.C. Prospects for the increased application of biocatalysts in organic transformations. Trends Biotechnol. 1993, 11, 461-470.
95. Dordick, J.S.; Khmelnitsky, Y.L.; Sergeeva, M.V. The evolution of biotransformation technologies. Curr. Opin. Microbiol. 1998, 1, 311-318.
96. Dordick, J.S. Biocatalysis in nonaqueous media. Patents and literature. Appl. Biochem. Biotech. 1988, 19, 103-112.
97. Pfromm, P.H.; Rezac, M.E.; Wurges, K.; Czermak, P. fumed silica activated subtilisin carlsberg in hexane in a packed-bed reactor. AIChE J. 2007, 53, 237-242.
98. Kallenberg, A.I.; Van Rantwijk, F.; Sheldon, R.A. Immobilization of Penicillin G acylase: the key to optimum performance. Adv. Synth. Catal. 2005, 347, 905-926.
99. Giordano, R.C.; Ribeiro, M.P.; Giordano, R.L. Kinetics of beta-lactam antibiotics synthesis by penicillin G acylase (PGA) from the viewpoint of the industrial enzymatic reactor optimization. Biotechnol. Adv. 2006, 24, 27-41.
100. Calleri, E.; Temporini, C.; Massolini, G.; Caccialanza, G. Penicillin G acylase-based stationary phases: Analytical applications. J. Pharm. Biomed. Anal. 2004, 35, 243-258.
101. Massolini, G.; Calleri, E.; De Lorenzi, E.; Pregnolato, M.; Terreni, M.; Felix, G.; Gandini, C. Immobilized penicillin G acylase as reactor and chiral selector in liquid chromatography. J. Chromatogr. A 2001, 921, 147-160.
102. Massolini, G.; Calleri, E.; Lavecchia, A.; Loiodice, F.; Lubda, D.; Temporini, C.; Fracchiolla, G.; Tortorella, P.; Novellino, E.; Caccialanza, G. Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column. Anal. Chem. 2003, 75, 535-542.
103. Pogori, N.; Xu, Y.; Cheikhyousseff, A. Potential aspects of lipases obtained from Rhizopus fungi. Res. J. Microbiol. 2007, 2, 101-116.
104. Ghanem, A.; Aboul-Enein, H.Y. Application of lipases in kinetic resolution of racemates. Chirality 2005, 17, 1-15.
105. Ghanem, A. Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 2007, 63, 1721-1754.
106. Dominguez de Maria, P.; Sinisterra, J.V.; Tsai, S.-W.; Alcantara, A.R. Carica papaya lipase (CPL): an emerging and versatile biocatalyst. Biotechnol. Adv. 2006, 24, 493-499.
107. Dominguez de Maria, P.; Carboni-Oerlemans, C.; Tuin, B.; Bargeman, G.; Van Der Meer, A.; Van Gemert, R. Biotechnological applications of Candida antarctica lipase A: state-of-the-art. J. Mol. Catal. B: Enzymatic 2005, 37, 36-46.
108. Villeneuve, P.; Muderhwa, J.M.; Graille, J.; Haas, M.J. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Mol. Catal. - B Enzymatic 2000, 9, 113-148.
109. Calleri, E.; Temporini, C.; Furlanetto, S.; Loiodice, F.; Fracchiolla, G.; Massolini, G. Lipases for biocatalysis: development of a chromatographic bioreactor. J. Pharm. Biomed. Anal. 2003, 32, 715-724.
110. Mullangi, R.; Yao, M.; Srinivas, N.R. Resolution of enantiomers of ketoprofen by HPLC: a review. Biomed. Chromatogr. 2003, 17, 423-434.
111. Jamali, F.; Brocks, D.R. Clinical pharmacokinetics of ketoprofen and its enantiomers. Clin. Pharmacokinet. 1990, 19, 197-217.
112. Ujang, Z.; Husain, W.H.; Seng, M.C.; Rashid, A.H.A. The kinetic resolution of 2-(4-chlorophenoxy) propionic acid using Candida rugosa lipase. Proc. Biochem. 2003, 38, 1483-1488.
113. Wedin, G.P.; Neal, J.S.; Everson, G.W.; Krenzelok, E.P. Castor bean poisoning. Am. J. Emerg. Med. 1986, 4, 259-261.
114. Challoner, K.R.; McCarron, M.M. Castor bean intoxication. Ann. Emerg. Med. 1990, 19, 1177-1183.
115. Biosensor. In IUPAC Compendium of Chemical Terminology; 1992; 148.
116. Fishman, H.A.; Greenwald, D.R.; Zare, R.N. Biosensors in chemical separations. Ann. Rev. Biophys. Biomol. Struct. 1998, 27, 165-198.