Enzyme-magnetic nanoparticle hybrids: New effective catalysts for the production of high value chemicals

Journal of Chemical Technology and Biotechnology

Volumn 87, Issue 5, 2012, Pages 583-594

  Yiu, Humphrey H P ^a   Keane, Mark A ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

Catalysis; Drug synthesis; Enzyme immobilization; Iron oxide; SPION magnetic nanoparticles

Indexed keywords

9 BETA DEXTRO ARABINOFURANOSYL GUANINE; ABACAVIR; ADENOSINE DEAMINASE; ANTIDIABETIC AGENT; ANTIHYPERTENSIVE AGENT; ANTIINFECTIVE AGENT; ANTILEUKEMIC AGENT; ANTINEOPLASTIC AGENT; ATAZANAVIR; CARBOVIR; CYTOCHROME P450; DOCETAXEL; ENTECAVIR; ENZYME; FOSINOPRIL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; INDINAVIR; LAMIVUDINE; LOBUCAVIR; MAGNETIC NANOPARTICLE; NATURAL PRODUCT; ORGANIC SOLVENT; PACLITAXEL; PREGABALIN; SAXAGLIPTIN; SQUALENE SYNTHASE INHIBITOR; TIGEMONAM; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZANAMIVIR;

BREAST CANCER; CANCER CHEMOTHERAPY; CATALYST; CATALYST SUPPORT; CHEMICAL REACTION; CHIRALITY; COST; DIABETES MELLITUS; DRUG INDUSTRY; DRUG MANUFACTURE; DRUG SYNTHESIS; ENZYME IMMOBILIZATION; GREEN CHEMISTRY; HEPATITIS B; HERPES SIMPLEX; HERPES VIRUS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HYPERCHOLESTEROLEMIA; HYPERTENSION; INFECTION; INFLUENZA A; INFLUENZA B; LEUKEMIA; LUNG CANCER; NANOMEDICINE; NANOTECHNOLOGY; NEUROPATHIC PAIN; NOTE; OVARY CANCER; RECYCLING; SYNTHESIS; VIRUS INFECTION;

EID: 84859427635     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.3735     Document Type: Note

References (90)

1. Patel RN, Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coordin Chem Rev 252: 659-701 (2008).
2. Wang P, Nanoscale biocatalyst systems. Curr Opinion Biotechnol 17: 574-579 (2006).
3. Zhao ZW, Lei W, Zhang XB, Wang BP and Jiang HL, ZnO-based amperometric enzyme biosensors. Sensors 10: 1216-1231 (2010).
4. 2 nanoparticle films on pyrolytic graphite electrodes: direct electrochemistry and bioelectrocatalysis. Electrochim Acta 49: 1981-1988 (2004).
5. Lee J, Kim J and Hyeon T, Recent progress in the synthesis of porous carbon materials. Adv Mater 18: 2073-2094 (2006).
6. Yiu HHP, Wright PA and Botting NP, Enzyme immobilization using SBA-15 mesoporous molecular sieves with functionalized surfaces. J Mol Catal B-Enzym 15: 81-92 (2001).
7. Yiu HHP, Engineering the multifunctional surface on magnetic nanoparticles for targeted biomedical applications: a chemical approach. Nanomedicine 6: 1429-1446 (2011).
8. Data from Fortune Global 500, The List, Fortune 160:(2009).
9. Sheldon RA, The E-factor: fifteen years on. Green Chem 9: 1273-1283 (2007).
10. Hanson RL, Goldberg SL, Brzozowski DB, Tully TP, Cazzulino D, Parker WL, et al, Preparation of an amino acid intermediate for the dipeptidyl peptidase IV inhibitor, saxagliptin, using a modified phenylalanine dehydrogenase. Adv Syn Cat 349: 1369-1378 (2007).
11. Xu ZM, Singh J, Schwinden MD, Zheng B, Kissick TP, Patel B, et al, Process research and development for an efficient synthesis of the HIV protease inhibitor BMS-232632. Org Proc Res Devel 6: 323-328 (2002).
12. Chartrain M, Jackey B, Taylor C, Sandfor V, Gbewonyo K, Lister L, et al, Bioconversion of indene to cis (1S, 2R) indandiol and trans (1R, 2R) indandiol by Rhodococcus species. J Ferment Technol 86: 550-558 (1998).
13. Buckland B, Robinson D and Chartrain M, Biocatalysis for pharmaceuticals-status and prospects for a key technology. Metab Eng 2: 42-48 (2000).
14. Mahmoudian M, Biocatalytic production of chiral pharmaceutical intermediates. Biocatal Biotransform 18: 105-118 (2000).
15. Hanson RL, Shi ZP, Brzozowski DB, Banerjee A, Kissick TP, Singh J, et al, Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug. Bioorg Med Chem 8: 2681-2687 (2000).
16. Patel RN, Banerjee A, Pendri YR, Liang J, Chen CP and Mueller R, Preparation of a chiral synthon for an HBV inhibitor: enzymatic asymmetric hydrolysis of (1-α, 2-β, 3-α)-2-(benzyloxymethyl)cyclopent-4-ene-1, 3-diol diacetate and enzymatic asymmetric acetylation of (1-α, 2-β, 3-α)-2-(benzyloxymethyl)cyclopent-4-ene-1, 3-diol. Tetrahedron Asymmetry 17: 175-178 (2006).
17. Mahmoudian M and Dawson MJ, Chemoenzymatic production of the antiviral agent Epivir in: Biotechnology of Antibiotics, ed. by Strohl WR. Marcel Dekker Inc., New York, 753-778 (1997).
18. Storer R, Clemens IR, Lamont B, Noble SA, Williamson C and Belleau B, The resolution and absolute stereochemistry of the enantiomers of cis-1-[2-(hydroxymethyl)-1, 3-oxathiolan-5-yl]cytosine (BCH189): Equipotent anti-HIV sgents. Nucleosides Nucleotides 12: 225-236 (1993).
19. Mahmoudian M, Baines BS, Drake CS, Hale RS, Jones P, Piercey JE, et al, Enzymatic production of optically pure (2' R-cis)-2'-deoxy-3'-thiacytidine (3TC, lamivudine): a potent anti-HIV agent Enzyme Microbiol Technol 15: 749-755 (1993).
20. Mahmoudian M, A decade of biocatalysis at Glaxo Wellcome in: Biocatalysis in the Pharmaceutical and Biotechnology Industries, ed. by Patel RN. CRC Press, Florida, pp. 53-102 (2007).
21. Holton RA, Somoza C, Kim HB, Liang F, Biediger RJ, Boatman PD, et al, First total synthesis of taxol. 1. Functionalization of the B ring. J Am Chem Soc 116: 1597-1598 (1994).
22. Holton RA, Kim HB, Somoza C, Liang F, Biediger RJ, Boatman PD, et al, First total synthesis of Taxol. 2. Completion of the C and D rings. J Am Chem Soc 116: 1599-1600 (1994).
23. Mahmoudian M, Development of bioprocesses for the generation of anti-inflammatory, anti-viral and anti-leukaemic agents, in Novel Frontiers in the Production of Compounds for Biomedical Use, ed. by van Broekhoven A, Shapiro F, Anné J, book series Focus Biotechnol 1. Kluwer Academic Publisher, Dordrecht, the Netherlands, pp. 249-265 (2001).
24. Matsuyama A, Yamamoto H and Kobayashi Y, Practical application of recombinant whole-cell biocatalysts for the manufacturing of pharmaceutical intermediates such as chiral alcohols. Org Process Res Devel 6: 558-561 (2002).
25. Lawrence M, Biller S and Fryszman O, Alpha-phosphonosulfinic squalene synthetase inhibitors. US Patent 5447922 (1995).
26. Hanson RL, Singh J, Kissick TP, Patel RN, Szarka LJ and Mueller RH, Synthesis of L-beta-hydroxyvaline from alpha-keto-beta-hydroxyisovalerate using leucine dehydrogenase from Bacillus species. Bioorg Chem 18: 116-130 (1990).
27. Patel RN, Robison RS and Szarka LJ, Stereoselective enzymatic hydrolysis of 2-cyclohexyl- and 2-phenyl-l, 3-propanediol diacetate in biphasic systems. Appl Microbiol Biotechnol 34: 10-14 (1990).
28. Xie Z, Feng J, Garcia E, Bernett M, Yazbeck D and Tao J, Cloning and optimization of a nitrilase for the synthesis of (3S)-3-cyano-5-methyl hexanoic acid. J Mol Catal B Enzym 41: 75-80 (2006).
29. List prices from Sigma Aldrich in 2011: semi-synthetic paclitaxel (>97%), GBP320.20 per 25 mg; gold puriss. powder (>99.999%), GBP172.70 per 1 g.
30. Ganem B and Franke RR, Paclitaxel from primary taxanes: a perspective on creative invention in organozirconium chemistry. J Org Chem 72: 3983-3987 (2007).
31. Malik S, Cusidó RM, Mirjalili MH, Moyano E, Palazón J and Bonfill M, Production of the anticancer drug taxol in Taxus baccata suspension cultures: a review. Process Biochem 46: 23-34 (2011).
32. Montalbetti CAGN and Falque V, Amide bond formation and peptide coupling. Tetrahedron 61: 10827-10852 (2005).
33. Parrado J and Bautista J, Immobilization-stabilization of Kerase. A senrine-protease from streptomyces-fradiae, by covalent attachment to porous-glass. Biosci Biotechnol Biochem 59: 906-907 (1995).
34. Iijima M, Matsuzaki T, Kadoya H, Hatahira S, Hiramatsu S, Jung G, et al, Bionanocapsule-based enzyme-antibody conjugates for enzyme-linked immunosorbent assay. Anal Biochem 396: 257-261 (2010).
35. Gill I and Patel R, Biocatalytic ammonolysis of (5S)-4, 5-dihydro-1H-pyrrole-1, 5-dicarboxylic acid, 1-(1, 1-dimethylethyl)-5-ethyl ester: preparation of an intermediate to the dipeptidyl peptidase IV inhibitor Saxagliptin. Bioorg Med Chem Lett 16: 705-709 (2006).
36. Kim MJ, Hennen WJ, Sweers HM and Wong CH, Enzymes in carbohydrate synthesis: N-acetylneuraminic acid aldolase catalyzed reactions and preparation of N-acetyl-2-deoxy-D-neuraminic acid derivatives. J Am Chem Soc 110: 6481-6486 (1988).
37. Patel RN, Banerjee A, Ko RY, Howell JM, Li WS, Comezoglu FT, et al, Enzymic preparation of (3R-cis)-3-(acetyloxy)-4-phenyl-2-azetidinone: a taxol side-chain synthon. Biotechnol Appl Biochem 20: 22-33 (1994).
38. Patel RN, Howell J, Chidambaram R, Benoit S and Kant J, Enzymatic preparation of (3R)-cis-3-acetyloxy-4-(1, 1-dimethylethyl)-2-azetidinone: a side-chain synthon for an orally active taxane. Tetrahedron Asymmetry 14: 3673-3677 (2003).
39. Zuffi G, Ghisotti D, Oliva I, Capra E, Frascotti G, Tonon G, et al, Immobilized biocatalysts for the production of nucleosides and nucleoside analogues by enzymatic transglycosylation reactions. Biocatal Biotransform 22: 25-33 (2004).
40. Homann M, Vail R, Morgan B, Sabesan V, Levy C, Dodds DR, et al, Enzymatic hydrolysis of a prochiral 3-substituted glutarate ester, an intermediate in the synthesis of an NK1/NK2 dual antagonist. Adv Synth Catal 343: 744-749 (2001).
41. Baldessari A and Mangone C, One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals. J Mol Catal B Enzym 11: 335-341 (2001).
42. Reetz MT, Zonta A and Simpelkamp J, Efficient immobilization of lipases by entrapment in hydrophobic sol-gel materials. Biotechnol Bioeng 49: 527-534 (1996).
43. Chiou SH and Wu WT, Immobilization of Candida rugosa lipase on chitosan with activation of the hydroxyl groups. Biomaterials 25: 197-204 (2004).
44. Ogino H and Ishikawa H, Enzymes which are stable in the presence of organic solvents. J Biosci Bioeng 91: 109-116 (2001).
45. Shakeri M, Engström K, Sandström AG and Bäckvall JE, Highly enantioselective resolution of beta-amino esters by Candida antarctica lipase A immobilized in mesocellular foam: application to dynamic kinetic resolution. Chem Catal Chem 2: 534-538 (2010).
46. Pencreach G, Leullier M and Baratti JC, Properties of free and immobilized lipase from Pseudomonas cepacia. Biotechnol Bioeng 56: 181-189 (1997).
47. Carta G, Gainer JL and Benton AH, Enzymatic synthesis of esters using an immobilized lipase. Biotechnol Bioeng 37: 1004-1009 (1991).
48. Mutua LN and Akoh CC, Synthesis of alkyl glycoside fattyacid esters in nonaqueous media by Candida sp. lipase. J Am Oil Chem Soc 70: 43-46 (1993).
49. Triantafyllou AO, Wehtje E, Adlercreutz P and Mattiasson B, How do additives affect enzyme activity and stability in nonaqueous media? Biotechnol Bioeng 54: 67-75 (1997).
50. Fernandez-Lafuente R, Armisen P, Sabuquillo P, Fernandez-Lorente G and Guisan JM, Immobilization of lipases by selective adsorption on hydrophobic supports. Chem Phys Lipid 93: 185-197 (1998).
51. Gemeiner P, Materials for enzyme engineering. In: Enzyme Engineering, ed. by Gemeiner P. Ellis Horwood, New York, pp. 13-119 (1992).
52. Fernandez-Lafuente R, Rodriguez V and Guisan JM, The coimmobilization of D-amino acid oxidase and catalase enables the quantitative transformation of D-amino acids (D-phenylalanine) into alpha-keto acids (phenylpyruvic acid). Enzyme Microbiol Technol 23: 28-33 (1998).
53. Matsuura S, Ishii R, Itoh T, Hanaoka T, Hamakawa S, Tsunoda T, et al, Direct visualization of hetero-enzyme co-encapsulated in mesoporous silicas. Micropor Mesopor Mater 127: 61-66 (2010).
54. Keighron JD and Keating C, Enzyme nanoparticle bioconjugates with two sequential enzymes: stoichiometry and activity of malate dehydrogenase and citrate synthase on Au nanoparticles. Langmuir 26: 18992-19000 (2010).
55. Katchalski-Katzir E, Immobilized enzymes-learning from past successes and failures. Trend Biotechnol 11: 471-478 (1993).
56. ® C, a carrier for immobilization of enzymes of industrial potential. J Mol Catal B Enzym 10: 157-176 (2000).
57. Bednarski MD, Chenault HK, Simon ES and Whitesides GM, Membrane-enclosed enzymatic catalysis (MEEC)-a useful, practical new method for the manipulation of enzymes in organic synthesis. J Am Chem Soc 109: 1283-1285 (1987).
58. Park HJ, McConnell JT, Boddohi S, Kipper MJ and Johnson PA, Synthesis and characterization of enzyme-magnetic nanoparticle complexes: effect of size on activity and recovery. Colloid Surf B-Biointerfaces 83: 198-203 (2011).
59. Chazelas C, Coudert JF, Jarrige J and Fauchais P, Synthesis of ultra fine particles by plasma transferred arc: influence of anode material on particle properties. J Eur Ceram Soc 26: 3499-3507 (2006).
60. Wu DB, Zhang L, Wang L, Zhu BH and Fan LY, Adsorption of lanthanum by magnetic alginate-chitosan gel beads. J Chem Technol Biotechnol 86: 345-352 (2011).
61. Okoli C, Boutonnet M, Mariey L, Järås S and Rajarao G, Application of magnetic iron oxide nanoparticles prepared from microemulsions for protein purification. J Chem Technol Biotechnol 86: 1386-1393 (2011).
62. Wang F, Guo C, Liu HZ and Liu CZ, Immobilization of Pycnoporus sanguineus laccase by metal affinity adsorption on magnetic chelator particles. J Chem Technol Biotechnol 83: 97-104 (2008).
63. Yiu HHP, Botting CH, Botting NP and Wright PA, Size selective protein adsorption on thiol-functionalized SBA-15 mesoporous molecular sieve. Phys Chem Chem Phys 3: 2983-2985 (2001).
64. Li L, Fan MH, Brown RC, Van Leeuwen JH, Wang JJ, Wang WH, et al, Synthesis, properties, and environmental applications of nanoscale iron-based materials: a review. Crit Rev Environ Sci Technol 36: 405-431 (2006).
65. 3 nanoparticles as potential MRI contrast agents. J Colloid Interface Sci 341: 248-254 (2010).
66. 4/amino-silane core-shell nanoparticles via layer-by-layer method. Appl Surf Sci 255: 7974-7980 (2009).
67. 4 nanoparticles for targeted bi-modal imaging of pancreatic cancer. J Mater Chem 21: 12650-12659 (2011).
68. Bouffier L, Yiu HHP and Rosseinsky MJ, Chemical grafting of a DNA intercalator probe onto functional iron oxide nanoparticles: a physicochemical study. Langmuir 27: 6185-6192 (2011).
69. Gill CS, Price BA and Jones CW, Sulfonic acid-functionalized silica-coated magnetic nanoparticle catalysts. J Catal 251: 145-152 (2007).
70. Matsunaga T and Kamiya S, Use of magnetic particles isolated from magnetotactic bacteria for enzyme immobilization. Appl Microbiol 26: 328-332 (1987).
71. Kobayashi H and Matsunaga T, Amino-silane modified superparamagnetic particles with surface-immobilized enzyme. J Colloid Interface Sci 141: 505-511 (1991).
72. Caruso F and Schuler C, Enzyme multilayers on colloid particles: assembly, stability, and enzymatic activity. Langmuir 16: 9595-9603 (2000).
73. Chien LJ and Lee CK, Biosilicification of dual-fusion enzyme immobilized on magnetic nanoparticle. Biotechnol Bioeng 100: 223-230 (2008).
74. Hsieh HC, Kuan IC, Lee SL, Tien GY, Wang YJ and Yu CY, Stabilization of D-amino acid oxidase from Rhodosporidium toruloides by immobilization onto magnetic nanoparticles. Biotechnol Lett 31: 557-563 (2009).
75. Sulek F, Drofenik M, Habulin M and Knez Ž, Surface functionalization of silica-coated magnetic nanoparticles for covalent attachment of cholesterol oxidase. J Magn Magn Mater 322: 179-185 (2010).
76. Shu B, Zheng G, Wei L and Yan S, Resolution of (+/-)-menthol by immobilized Candida rugosa lipase on superparamagnetic nanoparticles. Food Chem 96: 1-7 (2006).
77. Jiang YY, Guo C, Xia HS, Mahmooda I, Liu CZ and Liu HZ, Magnetic nanoparticles supported ionic liquids for lipase immobilization: enzyme activity in catalyzing esterification. J Mol Catal B Enzym 58: 103-109 (2009).
78. Yilmaz E, Sezgin M and Yilmaz M, Immobilization of Candida rugosa lipase on magnetic sol-gel composite supports for enzymatic resolution of (R, S)-Naproxen methyl ester. J Mol Catal B Enzym 69: 35-41 (2011).
79. Chaubey A, Parshad R, Taneja SC and Qazi GN, Arthrobacter sp. lipase immobilization on magnetic sol-gel composite supports for enantioselectivity improvement. Process Biochem 44: 154-160 (2009).
80. Hu B, Pan J, Yu HL, Liu JW and Xu JH, Immobilization of Serratia marcescens lipase onto amino-functionalized magnetic nanoparticles for repeated use in enzymatic synthesis of Diltiazem intermediate. Process Biochem 44: 1019-1024 (2009).
81. Dave R and Madamwar D, Esterification in organic solvents by lipase immobilized in polymer of PVA-alginate-boric acid. Process Biochem 41: 951-955 (2006).
82. Wang W, Xu Y, Wang DIC and Li Z, Recyclable nanobiocatalyst for enantioselective sulfoxidation: facile fabrication and high performance of chloroperoxidase-coated magnetic nanoparticles with iron oxide core and polymer shell. J Am Chem Soc 131: 12892-12893 (2009).
83. Ying M and Chen GY, Study on the production of biodiesel by magnetic cell biocatalyst based on lipase-producing Bacillus subtilis. Appl Biochem Biotechnol 137: 793-803 (2007).
84. Miltenyi S, Müller W, Weichel W and Radbruch A, High gradient magnetic cell separation with MACS. Cytometry 11: 231-238 (1990).
85. Gijs MAM, Magnetic bead handling on-chip: new opportunities for analytical applications. Microfluid Nanofluid 1: 22-40 (2004).
86. Bahaj AS, James PAB and Moeschler FD, High gradient magnetic separation of motile and non-motile magnetotactic bacteria. IEEE Trans Magnet 32: 5106-5108 (1996).
87. Cudjoe KS, Krona R and Olsen E, IMS: a new selective enrichment technique for detection of Salmonella in foods. Int J Food Microbiol 23: 159-165 (1994).
88. 4 nanocrystals. Science 314: 964-967 (2006).
89. Data published from the Department of Health, UK, (2009).
90. Steinbrook R, The price of sight-Ranibizumab, Bevacizumab, and the treatment of macular degeneration. New Engl J Med 355: 1409-1412 (2006).