Biocatalytic ketone reduction: A green and efficient access to enantiopure alcohols

Biotechnology Advances

Volumn 30, Issue 6, 2012, Pages 1279-1288

  Ni, Yan ^a   Xu, Jian He ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric reduction; Biocatalysis; Chiral alcohols; Genome mining; Reductases

Indexed keywords

ASYMMETRIC REDUCTION; BIOCATALYSIS; CHIRAL ALCOHOLS; GENOME MINING; REDUCTASES;

CHEMICAL INDUSTRY; KETONES; LOADING; ORGANIC COMPOUNDS;

STEREOCHEMISTRY;

ALCOHOL DERIVATIVE; KETONE;

AGROCHEMICAL; ALCOHOL; BIOTECHNOLOGY; CATALYSIS; CHEMICAL INDUSTRY; ENZYME ACTIVITY; GENOMICS; KETONE; PHARMACEUTICAL INDUSTRY;

BIOCATALYSIS; CHEMISTRY; GREEN CHEMISTRY; METABOLISM; METHODOLOGY; OXIDATION REDUCTION REACTION; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; BIOCATALYSIS; GREEN CHEMISTRY TECHNOLOGY; KETONES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84861474748     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2011.10.007     Document Type: Review

References (82)

1. Andrade L.H., Piovan L., Pasquini M.D. Improving the enantioselective bioreduction of aromatic ketones mediated by Aspergillus terreus and Rhizopus oryzae: the role of glycerol as a co-solvent. Tetrahedron: Asymmetry 2009, 20:1521-1525.
2. Ankati H., Zhu D., Yang Y., Biehl E.R., Hua L. Asymmetric synthesis of both antipodes of β-hydroxy nitriles and β-hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis. J Org Chem 2009, 74:1658-1662.
3. Applegate G.A., Cheloha R.W., Nelson D.L., Berkowitz D.B. A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: dynamic reductive kinetic resolution entry into the Taxotère side chain. Chem Commun 2011, 47:2420-2422.
4. Asako H., Shimizu M., Itoh N. Engineering of NADPH-dependent aldo-keto reductase from Penicillium citrinum by directed evolution to improve thermostability and enantioselectivity. Appl Microbiol Biotechnol 2008, 80:805-812.
5. Avni D., Braun S., Lev O., Ottolenghi M. Enzymes and other proteins entrapped in sol-gel materials. Chem Mater 1994, 6:1605-1614.
6. Baer K., Krauβer Ma, Burda E., Hummel W., Berkessel A., Gröger H. Sequential and modular synthesis of chiral 1, 3-diols with two stereogenic centers: access to all four stereoisomers by combination of organo- and biocatalysis. Angew Chem Int Ed 2009, 48:9355-9358.
7. Bhattacharyya M.S., Singh A., Banerjee U.C. Immobilization of intracellular carbonyl reductase from Geotrichum candidum for the stereoselective reduction of 1-naphthyl ketone. Bioresour Technol 2010, 101:1581-1586.
8. Blanchard L.A., Brennecke J.F. Recovery of organic products from ionic liquids using supercritical carbon dioxide. Ind Eng Chem Res 2001, 40:287-292.
9. Bommarius A.S., Riebel B.R. Biocatalysis: fundamentals and applications 2004, Wiley-VCH, Weinheim.
10. Bommarius A.S., Blum J.K., Abrahamson M.J. Status of protein engineering for biocatalysts: how to design an industrially useful biocatalyst. Curr Opin Chem Biol 2011, 15:194-200.
11. Bornscheuer U.T. Immobilizing enzymes: how to create more suitable biocatalysts. Angew Chem Int Ed 2003, 42:3336-3337.
12. Braütigam S., Bringer-Meyer S., Weuster-Botz D. Asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems by use of recombinant Escherichia coli with intracellular cofactor regeneration. Tetrahedron: Asymmetry 2007, 18:1883-1887.
13. Braütigam S., Dennewald D., Schürmann M., Lutje-Spelberg J., Pitner W.R., Weuster-Botz D. Whole-cell biocatalysis: evaluation of new hydrophobic ionic liquids for efficient asymmetric reduction of prochiral ketones. Enzyme Microb Technol 2009, 45:310-316.
14. Burda E., Hummel W., Gröger H. Modular chemoenzymatic one-pot syntheses in aqueous media: combination of a palladium-catalyzed cross-coupling with an asymmetric biotransformation. Angew Chem Int Ed 2008, 47:9551-9554.
15. Campbell E., Wheeldon I.R., Banta S. Broadening the cofactor specificity of a thermostable alcohol dehydrogenase using rational protein design introduces novel kinetic transient behavior. Biotechnol Bioeng 2010, 107:763-774.
16. Cantone S., Hanefeld U., Basso A. Biocatalysis in non-conventional media-ionic liquids, supercritical fluids and the gas phase. Green Chem 2007, 9:954-971.
17. Carballeira J.D., Quezada M.A., Hoyos P., Simeó Y., Hernaiz M.J., Alcantara A.R., et al. Microbial cells as catalysts for stereoselective red-ox reactions. Biotechnol Adv 2009, 27:686-714.
18. Cuetos A., Valenzuela M.L., Lavandera I., Gotor V., Carriedo G.A. Polyphosphazenes as tunable and recyclable supports to immobilize alcohol dehydrogenases and lipases: synthesis, catalytic activity, and recycling efficiency. Biomacromolecules 2010, 11:1291-1297.
19. de Gonzalo G., Lavandera I., Faber K., Kroutil W. Enzymatic reduction of ketones in "micro-aqueous" media catalyzed by ADH-A from Rhodococcus ruber. Org Lett 2007, 9:2163-2166.
20. de María P.D., Mauger Z. Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents. Curr Opin Chem Biol 2011, 15:220-225.
21. de Wildeman S.M.A., Sonker T., Schoemaker H.E., May O. Biocatalytic reductions: from lab curiosity to "first choice". Acc Chem Res 2007, 40:1260-1266.
22. Demir A.S., Talpur F.N., Sopaci S.B., Kohring G.-W., Celik A. Selective oxidation and reduction reactions with cofactor regeneration mediated by galactitol-, lactate-, and formate dehydrogenases immobilized on magnetic nanoparticles. J Biotechnol 2011, 152:176-183.
23. Dennewalda D., Pitnerb W.-R., Weuster-Botza D. Recycling of the ionic liquid phase in process integrated biphasic whole-cell biocatalysis. Process Biochem 2011, 46:1132-1137.
24. Fox R.J., Davis S.C., Mundorff E.C., Newman L.M., Gavrilovic V., Ma S.K., et al. Improving catalytic function by ProSAR-driven enzyme evolution. Nat Biotechnol 2007, 25:338-344.
25. Gauchot G., Kroutil W., Schmitzer A.R. Highly recyclable chemo-/biocatalyzed cascade reactions with ionic liquids: one-pot synthesis of chiral biaryl alcohols. Chem Eur J 2010, 16:6748-6751.
26. Gennaro P.D., Bernasconi S., Orsini F., Corretto E., Sello G. Multienzymatic preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid. Tetrahedron: Asymmetry 2010, 21:1885-1889.
27. Goldberg K., Schroer Kirsten, Lütz S., Liese A. Biocatalytic ketone reduction - a powerful tool for the production of chiral alcohols - part I: processes with isolated enzymes. Appl Microbiol Biotechnol 2007, 76:237-248.
28. Gorke J., Srienc F., Kazlauskas R. Towards advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol Bioprocess Eng 2010, 15:40-53.
29. Gröger H., Chamouleau F., Orologas N., Rollmann C., Drauz K., Hummel W., et al. Enantioselective reduction of ketones with "designer cells" at high substrate concentrations: highly efficient access to functionalized optically active alcohols. Angew Chem Int Ed 2006, 45:5677-5681.
30. Hammond J.R., Poston W.B., Ghiviriga I., Feske D.B. Biocatalytic synthesis towards both antipodes of 3-hydroxy-3-phenylpropanitrile, a precursor to fluoxetine, atomoxetine and nisoxetine. Tetrahedron Lett 2007, 48:1217-1219.
31. Harada T., Kubota Y., Kamitanaka T., Nakamura K., Matsuda T. A novel method for enzymatic asymmetric reduction of ketones in a supercritical carbon dioxide/water biphasic system. Tetrahedron Lett 2009, 50:4934-4936.
32. He J.Y., Zhou L.M., Wang P., Zu L. Microbial reduction of ethyl acetoacetate to ethyl (R)-3-hydroxybutyrate in an ionic liquid containing system. Process Biochem 2009, 44:316-321.
33. Hernáiz M.J., Alcántara A.R., García J.I., Sinisterra J.V. Applied biotransformations in green solvents. Chem Eur J 2010, 16:9422-9437.
34. Hildebrand F., Lütz S. Immobilisation of alcohol dehydrogenase from Lactobacillus brevis and its application in a plug-flow reactor. Tetrahedron: Asymmetry 2006, 17:3219-3225.
35. Hollmann F., Arends I.W.C.E., Buehler K. Biocatalytic redox reactions for organic synthesis: nonconventional regeneration methods. ChemCatChem 2010, 2:762-782.
36. Hollmann F., Arends I.W.C.E., Holtmann D. Enzymatic reductions for the chemist. Green Chem 2011, 13:2285-2313.
37. Hölsch K., Weuster-Botz D. New oxidoreductases from cyanobacteria: exploring nature's diversity. Enzyme Microb Technol 2010, 47:228-235.
38. Huisman G.W., Liang J., Krebber A. Practical chiral alcohol manufacture using ketoreductase. Curr Opin Chem Biol 2010, 14:122-1129.
39. Hussain W., Pollard D.J., Truppo M., Lye G.J. Enzymatic ketone reductions with co-factor recycling: improved reactions with ionic liquid co-solvents. J Mol Catal B: Enzym 2008, 55:19-29.
40. Itoh N., Nakamura M., Inoue K., Makino Y. Continuous production of chiral 1, 3-butanediol using immobilized biocatalysts in a packed bed reactor: promising biocatalysis method with an asymmetric hydrogen-transfer bioreduction. Appl Microbiol Biotechnol 2007, 75:1249-1256.
41. Kalaitzakis D., Smono I. A two-step, one-pot enzymatic synthesis of 2-substituted 1, 3-diols. J Org Chem 2010, 75:8658-8661.
42. Kaluzna I.A., Matsuda T., Sewell A.K., Stewart J.D. Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions. J Am Chem Soc 2004, 126:12827-12832.
43. Kaluzna I.A., Feske B.D., Wittayanan W., Ghiviriga I., Stewart J.D. Stereoselective, biocatalytic reductions of α-chloro-β-keto esters. J Org Chem 2005, 70:342-345.
44. Kansal H., Banerjee U.C. Enhancing the biocatalytic potential of carbonyl reductase of Candida viswanathii using aqueous-organic solvent system. Bioresour Technol 2009, 100:1041-1047.
45. Kohlmann C., Leuchs S., Greiner L., Leitner W. Continuous biocatalytic synthesis of (R)-2-octanol with integrated product separation. Green Chem 2011, 13:1430-1436.
46. Kohlmanna C., Robertza N., Leuchsa S., Dogana Z., Lütz S., Bitzer K., et al. Ionic liquid facilitates biocatalytic conversion of hardly water soluble ketones. J Mol Catal B: Enzym 2011, 68:147-153.
47. Kurbanoglu E.B., Zilbeyaz K., Ozdal M., Taskin M., Kurbanoglu N.I. Asymmetric reduction of substituted acetophenones using once immobilized Rhodotorula glutinis cells. Bioresour Technol 2010, 101:3825-3829.
48. Kurbanoglu E.B., Zilbeyaz K., Kurbanoglu N.I., Ozdal M., Taskin M., Algur O.F. Continuous production of (S)-1-phenylethanol by immobilized cells of Rhodotorula glutinis with a specially designed process. Tetrahedron: Asymmetry 2010, 21:461-464.
49. Laane C., Boeren S., Vos K., Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 1987, 30:81-87.
50. León R., Fernandes P., Pinheiro H.M., Cabral J.M.S. Whole-cell biocatalysis in organic media. Enzyme Microb Technol 1998, 23:483-500.
51. Li Y.L., Xu J.H., Xu Y. Deracemization of aryl secondary alcohols via enantioselective oxidation and stereoselective reduction with tandem whole-cell biocatalysts. J Mol Catal B: Enzym 2010, 64:48-52.
52. Li H.M., Yang Y., Zhu D.M., Hua L., Kantardjieff K. Highly enantioselective mutant carbonyl reductases created via structure-based site-saturation mutagenesis. J Org Chem 2010, 75:7559-7564.
53. Liang J., Lalonde J., Borup B., Mitchell V., Mundorff E., Trinh N., et al. Development of a biocatalytic process as an alternative to the (-)-DIP-Cl-mediated asymmetric reduction of a key intermediate of montelukast. Org Proc Res Dev 2010, 14:193-198.
54. Liang J., Mundorff E., Voladri R., Jenne S., Gilson L., Conway A., et al. Highly enantioselective reduction of a small heterocyclic ketone: biocatalytic reduction of tetrahydrothiophene-3-one to the corresponding (R)-alcohol. Org Proc Res Dev 2010, 14:188-192.
55. Liu W., Zhang S., Wang P. Nanoparticle-supported multi-enzyme biocatalysis with in situ cofactor regeneration. J Biotechnol 2009, 139:102-107.
56. Ma S.K., Gruber J., Davis C., Newman L., Gray D., Wang A., et al. A green-by-design biocatalytic process for atorvastatin intermediate. Green Chem 2010, 12:81-86.
57. Machielsen R., Leferink N.G.H., Hendriks A., Brouns S.J.J., Hennemann H.-G., Dauβmann T., et al. Laboratory evolution of Pyrococcus furiosus alcohol dehydrogenase to improve the production of (2S, 5S)-hexanediol at moderate temperatures. Extremophiles 2008, 12:587-594.
58. Musa M.M., Ziegelmann-Fjeld K.I., Vieille C., Zeikus J.G., Phillips R.S. Xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus performs asymmetric reduction of hydrophobic ketones in organic solvents. Angew Chem Int Ed 2007, 46:3091-3094.
59. Matsuda T., Yamanaka R., Nakamura K. Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron:Asymmetry 2009, 20:513-557.
60. Musa M.M., Lott N., Laivenieks M., Watanabe L., Vieille C., Phillips R.S. A single point mutation reverses the enantiopreference of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase. ChemCatChem 2009, 1:89-93.
61. Mutti F.G., Orthaber A., Schrittwieser J.H., de Vries J.G., Pietschnig R., Kroutil W. Simultaneous iridium catalysed oxidation and enzymatic reduction employing orthogonal reagents. Chem Commun 2010, 46:8046-8048.
62. Ni Y., Li C.X., Ma H.M., Zhang J., Xu J.H. Biocatalytic properties of a recombinant aldo-keto reductase with broad substrate spectrum and excellent stereoselectivity. Appl Microbiol Biotechnol 2011, 89:1111-1118.
63. Ni Y., Li C.X., Wang L.J., Zhang J., Xu J.H. Highly stereoselective reduction of prochiral ketones by a bacterial reducatse coupled with cofactor regeneration. Org Biomol Chem 2011, 9:5463-5468.
64. -1 by a bacterial reductase with broad substrate spectrum. Adv Synth Catal 2011, 353:1213-1217.
65. Nie Y., Xiao R., Xu Y., Montelione G.T. Novel anti-Prelog stereospecific carbonyl reductases from Candida parapsilosis for asymmetric reduction of prochiral ketones. Org Biomol Chem 2011, 9:4070-4078.
66. Pennacchio A., Pucci B., Secundo F., Cara F.L., Rossi M. Raia1 CA. Purification and characterization of a novel recombinant highly enantioselective short-chain NAD(H)-dependent alcohol dehydrogenase from Thermus thermophilus. Appl Environ Microbiol 2008, 74:3949-3958.
67. Quijano G., Couvert A., Amrane A. Ionic liquids: applications and future trends in bioreactor technology. Bioresour Technol 2010, 101:8923-8930.
68. Rao N.N., Lütz S., Würges K., Minör D. Continuous biocatalytic processes. Org Proc Res Dev 2009, 13:607-616.
69. Schrittwieser J.H., Sattler J., Resch V., Mutti F.G., Kroutil W. Recent biocatalytic oxidation-reduction cascades. Curr Opin Chem Biol 2011, 15:249-256.
70. Schroer K., Lütz S. A continuously operated bimembrane reactor process for the biocatalytic production of (2R, 5R)-hexanediol. Org Proc Res Dev 2009, 13:1202-1205.
71. Schroer K., Mackfeld U., Tan I.A.W., Wandrey C., Heuser F., Bringer-Meyer S., et al. Continuous asymmetric ketone reduction processes with recombinant Escherichia coli. J Biotechnol 2007, 132:438-444.
72. Sheldon R.A. Enzyme immobilization: the quest for optimum performance. Adv Synth Catal 2007, 349:1289-1307.
73. Szymanski W., Postema C.P., Tarabiono C., Berthiol F., Campbell-Verduyn L., De Wildeman S., et al. Combining designer cells and click chemistry for a one-pot four-step preparation of enantiopure β-hydroxytriazoles. Adv Synth Catal 2010, 352:2111-2115.
74. Valadez-Blanco R., Livingston A.G. Enantioselective whole-cell biotransformation of acetophenone to S-phenylethanol by Rhodotorula glutinis. Part II. Aqueous-organic systems: emulsion and membrane bioreactors. Biochem Eng J 2009, 46:54-60.
75. Voss C.V., Gruber C.C., Faber K., Knaus T., Macheroux P., Kroutil W. Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols. J Am Chem Soc 2008, 130:13969-13972.
76. Wang L.J., Li C.X., Ni Y., Zhang J., Liu X., Xu J.H. Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor. Bioresour Technol 2011, 102:7023-7028.
77. Wolfson A., Dlugya C., Tavora D., Blumenfelda J., Shotland Y. Baker's yeast catalyzed asymmetric reduction in glycerol. Tetrahedron: Asymmetry 2006, 17:2043-2045.
78. Wu X.R., Chen C., Liu N., Chen Y.J. Preparation of ethyl 3R, 5S-6-(benzyloxy)-3, 5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system. Bioresour Technol 2011, 102:3649-3652.
79. Xie Y., Xu J.H., Xu Y. Isolation of a Bacillus strain producing ketone reductase with high substrate tolerance. Bioresour Technol 2010, 101:1054-1059.
80. Zhang R.Z., Xu Y., Sun Y., Zhang W.C., Xiao R. Ser67Asp and His68Asp substitutions in Candida parapsilosis carbonyl reductase alter the coenzyme specificity and enantioselectivity of ketone reduction. Appl Environ Microbiol 2009, 75:2176-2183.
81. Zhao H., van der Donk W.A. Regeneration of cofactors for use in biocatalysis. Curr Opin Biotechnol 2003, 14:583-589.
82. Zhu D., Yang Y., Majkowicz S., Pan T.H., Kantardjieff K., Hua L. Inverting the enantioselectivity of an carbonyl reductase via substrate-enzyme docking-guided point mutation. Org Lett 2008, 10:525-528.