Candida spp. redox machineries: An ample biocatalytic platform for practical applications and academic insights

Biotechnology Advances

Volumn 27, Issue 3, 2009, Pages 278-285

  Gamenara, Daniela ^a   Domínguez de María, Pablo ^b  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

Author keywords

Biocatalysis; Candida; Deracemizations; Oxidations; Oxidoreductases; Reductions

Indexed keywords

BIOCATALYSIS; BIOCATALYTIC APPLICATIONS; CANDIDA; CATALYTIC MECHANISMS; CHIRAL BUILDING BLOCKS; COFACTORS; DERACEMIZATIONS; ENANTIO; FUNDAMENTAL RESEARCHES; OXIDOREDUCTASES; SACRIFICIAL SUBSTRATES;

BIOCHEMISTRY; CATALYSTS; INDUSTRIAL APPLICATIONS; MACHINERY; NITROGEN COMPOUNDS; OXIDATION;

ENZYMES;

FUNGAL PROTEIN; OXIDOREDUCTASE;

CATALYSIS; ENZYME ACTIVITY; FUNGUS; OXIDATION; REDUCTION;

BIOCATALYSIS; BIOTECHNOLOGY; CANDIDA; ENZYMOLOGY; METABOLISM; REVIEW;

BIOCATALYSIS; BIOTECHNOLOGY; CANDIDA; FUNGAL PROTEINS; OXIDOREDUCTASES;

CANDIDA;

EID: 60849109478     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2009.01.005     Document Type: Review

References (92)

1. Arnone A., Biagini G., Cardillo R., Resnati G., Begue J.P., Bonnet-Delpon D., et al. Microbial reduction of α,α,α-trifluoro-α'-sulfenylketones. Tetrahedron Lett 37 (1996) 3903-3906
2. Baskar B., Pandian N.G., Priya K., and Chadha A. Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and but-3-enoates by Candida parapsilosis ATCC 7330: assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR. Tetrahedron: Asymmetry 15 (2004) 3961-3966
3. Baskar B., Pandian N.G., Priya K., and Chadha A. Deracemisation of aryl substituted a-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism. Tetrahedron 61 (2005) 12296-12306
4. Beloqui A., Dominguez de Maria P., Golyshin M., and Ferrer M. Recent trends in industrial microbiology. Curr Opin Microbiol 11 (2008) 240-248
5. Bornscheuer U.T., and Kazlauskas R.J. Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew Chem Int Ed 43 (2004) 6032-6040
6. Buchholz S., and Gröger H. Enantioselective biocatalytic reduction of ketones for the synthesis of optically pure alcohols. In: Patel R.N. (Ed). Biocatalysis in the pharmaceutical and biotechnology industries (2006), Taylor & Francis, New York 757-790
7. Carboni-Oerlemans C., Dominguez de Maria P., Tuin B., Bargeman G., van der Meer A., and van Gemert R. Hydrolase-catalysed synthesis of peroxycarboxylic acids: biocatalytic promiscuity for practical applications. J Biotechnol 126 (2006) 140-151
8. Chadha A., and Baskar B. Biocatalytic deracemisation of a-hydroxy esters: high yield preparation of (S)-ethyl 2-hydroxy-4-phenylbutanoate from the racemate. Tetrahedron: Asymmetry 13 (2002) 1461-1464
9. Chartrain M., Mathre D., Reamer R.A., Patel S., Shinkal I., and Greasham R. Asymmetric bioreduction of cyclohexylphenyl ketone to its corresponding alcohol (+) cyclohexylphenyl alcohol by the yeast Candida magnoliae MY 1785. J Ferment Bioeng 83 (1997) 395-396
10. Chartrain M., Roberge C., Chung J., McNamara J., Zhao D., Olewinski R., et al. Asymmetric bioreduction of (2-(4-nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide) to its corresponding (R) alcohol [(R)-N- (2-hydroxy-2-pyridin-3-yl-ethyl)-2-(4-nitro-phenyl)-acetamide) by using Candida sorbophila MY 1833. Enzyme Microb Technol 25 (1999) 489-496
11. Chen Y., Lin H., Xu X., Xia S., and Wang L. Preparation the key intermediate of angiotensin-converting enzyme (ACE) inhibitors: high enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21. Adv Synth Catal 350 (2008) 426-430
12. Cheng C., and Ma J.-H. Glucose metabolism and bioreduction of 2-butanone by Candida utilis studied by means of ion-exchange chromatography. J Chromatograph A 20th International symposium on high performance liquid phase separations and related techniques vol. 763 (1997) 205-211
13. De Wildeman S.M.A., Sonke T., Schoemaker H.E., and May O. Biocatalytic reductions: from lab curiosity to "first choice". Acc Chem Res 40 (2007) 1260-1266
14. Dominguez de Maria P. Influencia de las condiciones de fermentación en la obtención de lipasas de Candida rugosa y en su actividad y enantioselectividad frente a reacciones orgánicas no convencionales (2002), Universidad Complutense, Madrid, España
15. Dominguez de Maria P., Sánchez-Montero J.M., Alcantara A.R., Valero F., and Sinisterra Gago J. Rational strategy for the production of new crude lipases from Candida rugosa. Biotechnol Lett 27 (2005) 499-503
16. Dominguez de Maria P., Sanchez-Montero J.M., Sinisterra J.V., and Alcantara A.R. Understanding Candida rugosa lipases: an overview. Biotechnol Adv 24 (2006) 180-196
17. Faber K. Biotransformations in organic chemistry. 5th ed. (2004), Springer Verlag, Berlin
18. Fatima Y., Kansal H., Soni P., and Banerjee U.C. Enantioselective reduction of aryl ketones using immobilized cells of Candida viswanathii. Proc Biochem 42 (2007) 1412-1418
19. Ferré E., N'guyen M., Le Petti J., and Gil G. Microbial oxidation of amines: a preliminary investigation on the resolution of racemic 1-phenylethylamine. Biocatal Biotransform 20 (2002) 311
20. Fuganti C., Grasselli P., Mendozza M., Servi S., and Zucchi G. Microbially-aided preparation of (S)-2-methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem. Tetrahedron 53 (1997) 2617-2624
21. Fujieda S., Tomita M., Fuhshuku K., Ohba S., Nishiyama S., and Sugai T. Chemoenzymatic route to both enantiomers of a 1-isopropyl-3a-methyloctahydroinden-4-one derivative: a synthetic intermediate for sesqui- and diterpenoids. Adv Synth Catal 347 (2005) 1099-1109
22. Gabor E., Liebeton K., Niehaus F., Eck J., and Lorentz P. Updating the metagenomics toolbox. Biotech J 2 (2007) 201-206
23. Goldberg K., Schroer K., Lütz S., and Liese A. Biocatalytic ketone reduction- a powerful tool for the production of chiral alcohols-part I: processes with isolated enzymes. Appl Microbiol Biotechnol 76 (2007) 237-248
24. Goldberg K., Schroer K., Lütz S., and Liese A. Biocatalytic ketone reduction-a powerful tool for the production of chiral alcohols-part II: whole-cell reductions. Appl Microbiol Biotechnol 76 (2007) 249-255
25. Goswami A., Mirfakhrae K.D., Totleben M.J., Swaminathan S., and Patel R.N. Microbial reduction of α-chloroketone to α-chlorohydrin. J Ind Microbiol Biotechnol 26 (2001) 259-262
26. Gröger H., Hummel W., Buchholz S., Drauz K., Van Nguyen T., Rollmann C., et al. Practical asymmetric enzymatic reduction through discovery of a dehydrogenase-compatible biphasic reaction media. Org Lett 5 (2003) 173-176
27. Gröger H., Chamouleau F., Orologas N., Rollmann C., Drauz K., Waldmann H., 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 45 (2006) 5677-5681
28. Hasegawa J., Ogura M., Tsuda S., Maemoto S., Kutsuki H., and Ohashi T. High-yield production of optically active 1,2-diols from the corresponding racemates. Agric Biol Chem 54 (1990) 1819-1827
29. Hilterhaus L., and Liese A. Building blocks. Adv Biochem Eng Biotechnol 105 (2007) 133-173
30. Hiraoka C., Matsuda M., Suzuki Y., Fujieda S., Tomita M., Fuhshuku K.-i., Obata R., Nishiyama S., and Sugai T. Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones. Tetrahedron: Asymmetry 17 (2006) 3358-3367
31. Hoyos P, Sinisterra Gago J, Dominguez de Maria P, Alcantara AR. in press. Hydrolase based synthesis of enantiopure a-hydroxyketones: from racemic resolutions to chemoenzymatic dynamic resolution. Biotechnology: Research, Technology and Applications. New York, USA: Nova Science Inc.: Accepted for publication.
32. Hult K., and Berglund P. Enzyme promiscuity: mechanism and applications. Trends Biotech 25 (2007) 231-238
33. Kataoka M., Doi Y., Sim T.S., Shimizu S., and Yamada H. A novel NADPH-dependent carbonyl reductase of Candida macedoniensis: purification and characterization. Arch Biochem Biophys 294 (1992) 469-474
34. Kavanagh K.L., Klimacek M., Nidetzky B., and Wilson D.K. The structure of Apo and Holo forms of xylose reductase, a dimeric aldo-keto reductase from Candida tenuis. Biochemistry 41 (2002) 8785-8795
35. Kavanagh K.L., Klimacek M., Nidetzky B., and Wilson D.K. Structure of xylose reductase bound to NAD+ and the basis for single and dual co-xubstrate specificity in family 2-aldo-keto reductases. Biochem J 373 (2003) 319-326
36. Kazlauskas R.J. Enhancing catalytic promiscuity for biocatalysis. Curr Opin Chem Biol 9 (2005) 195-201
37. Koul S., Crout D.H.G., Errington W., and Tax J. Biotransformation of α,β-unsaturated carbonyl compounds: sulfides, sulfoxides, sulfones, nitriles and esters by yeast species: carbonyl group and carbon-carbon double bond reduction. J Chem Soc Perkin I 23 (1995) 2969-2988
38. Kratzer R., Kavanagh K.L., Wilson D.K., and Nidetzky B. Studies of the enzymic mechanism of Candida tenuis xylose reductase (AKR 2B5): X-ray structure and catalytic reaction profile for the H113A mutant. Biochemistry 43 (2004) 4944-4954
39. Kratzer R., Leitgeb S., Wilson D.K., and Nidetzky B. Probing the substrate binding site of Candida tenuis xylose reductase (AKR2B5) with site-directed mutagenesis. Biochem J 393 (2006) 51-58
40. Kratzer R., and Nidetzky B. Identification of Candida tenuis xylose reductase as highly selective biocatalyst for the synthesis of aromatic alpha-hydroxy esters and improvement of its efficiency by protein engineering. Chem Commun 10 (2007) 1047-1049
41. Liese A., Zelinski T., Kula M.R., Kierkels H., Karutz M., Kragl U., et al. A novel reactor concept for the enzymatic reduction of poorly soluble ketones. J Mol Catal B: Enzym 4 (1998) 91-99
42. Liese A., Seebach K., and Wandrey C. Industrial biotransformations. 2nd. ed. (2006), Wiley-VCH, Weinheim
43. Lorentz P., and Eck J. Metagenomics and industrial applications. Nature Rev Microbiol 3 (2005) 510-516
44. Matsuyama A., Yamamoto H., Kawada N., and Kobayashi Y. Industrial production of (R)-1,3-butanediol by new biocatalysts. J Mol Catal B: Enzym 11 (2001) 513-521
45. Mauersberger S., Drechsler H., Oehme G., and Müller H.G. Substrate specificity and stereoselectivity of fatty alcohol oxidase from the yeast Candida maltosa. Appl Microbiol Biotechnol 37 (1992) 66-73
46. Mayr P., and Nidetzky B. Catalytic reaction profile for NADH-dependent reduction of aromatic aldehydes by xylose reductase from Candida tenuis. Biochem J 366 (2002) 889-899
47. Mayr P., Brüggler K., Kulbe K.D., and Nidetzky B. D-xylose metabolism by Candida intermedia: isolation and characterisation of two forms of aldose reductase with different coenzyme specificities. J Chromatogr B 737 (2000) 195-202
48. Molinari F., Gandolfi R., Villa R., and Occhiato E.G. Lyophilised yeasts: easy-to-handle biocatalysts for stereoselective reduction of ketones. Tetrahedron: Asymmetry 10 (1999) 3515-3520
49. Morikawa S., Nakai T., Yasohara Y., Nanba H., Kizaki N., and Hasegawa J. Highly active mutants of carbonyl reductase S1 with inverted coenzyme specificity and production of optically active alcohols. Biosci Biotechnol Biochem 69 (2005) 544-552
50. Mu X.Q., Xu Y., Nie Y., Ouyang J., and Sun Z.H. Candida parapsilosis CCTCC M203011 and the optimization of fermentation medium for stereoinversion of (S)-1-phenyl-1,2-ethanediol. Proc Biochem 40 (2005) 2345-2350
51. Nakamura K., Yamanaka R., Matsuda T., and Harada T. Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asymmetry 14 (2003) 2659-2681
52. Nath A., and Atkins W.M. A quantitative index of substrate promiscuity. Biochemistry 47 (2008) 157-166
53. Nestl B.M., Voss C.V., Bodlenner A., Ellmer-Schaumberger U., Kroutil W., and Faber K. Biocatalytic racemization of sec-alcohols and α-hydroxyketones using lyophilized microbial cells. Appl Microbiol Biotechnol 76 (2007) 1001-1008
54. Nuehauser W., Haltrich D., Kulbe K.D., and B. N. NAD(P)H-dependent aldose reductase from the xylose-assimilating yeast Candida tenuis. Isolation, characterization and biochemical properties of the enzyme. Biochem J. 326 (1997) 683-692
55. Nidetzky B., Klimacek M., and Mayr P. Transient-state and steady-state kinetic studies of the mechanism of NADH-dependent aldehyde reduction catalyzed by xylose reductase from the yeast Candida tenuis. Biochemistry 40 (2001) 10371-10381
56. Nie Y., Xu Y., and Mu X.Q. Highly enantioselective conversion of racemic 1-phenyl-1,2-ethanediol by stereoinversion involving a novel cofactor-dependent oxidoreduction system of Candida parapsilosis CCTCC M203011. Org Process Res Dev 8 (2004) 246-251
57. Nie Y., Xu Y., Qing Mu X., Tang Y., Jiang J., and Hao Sun Z. High-yield conversion of (R)-2-octanol from the corresponding racemate by stereoinversion using Candida rugosa. Biotechnol Lett 27 (2005) 23-26
58. Nie Y., Xu Y., Yang M., and Mu X.Q. A novel NADH-dependent carbonyl reductase with unusual stereoselectivity for (R)-specific reduction from an (S)-1-phenyl-1,2-ethanediol-producing micro-organism: purification and characterization. Lett Appl Microbiol 44 (2007) 555-562
59. Pacheco A.O., Kagohara E., Andrade L.H., Comasseto J.V., Crusius I.H.S., Paula C.R., et al. Biotransformations of nitro-aromatic compounds to amines and acetamides by tuberous roots of Arracacia xanthorrhiza and Beta vulgaris and associated microorganism (Candida guilliermondii). Enzyme Microb Technol 42 (2007) 65-69
60. Padhi S.K., and Chadha A. Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR. Tetrahedron: Asymmetry 16 (2005) 2790-2798
61. Padhi S.K., Pandian N.G., and Chadha A. Microbial deracemisation of aromatic β-hydroxy acid esters. J Mol Catal B: Enz. Proceedings of the 6th International Symposium on Biocatalysis and Biotransformations - BIOTRANS'03 vol. 29 (2004) 25-29
62. Padhi S.K., Titu D., Pandian N.G., and Chadha A. Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation. Tetrahedron 62 (2006) 5133-5140
63. Patel R.N. Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coord Chem Rev 252 (2008) 659-701
64. Patel R.N., Hou C.T., Laskin A.I., Derelanko P., and Felix A. Microbial production of methyl ketones purification and properties of a secondary alcohol dehydrogenase from yeast. Eur J Biochem 101 (1979) 401-406
65. Peters J., Zelinski T., and Kula M.R. Studies on the distribution and regulation of microbial keto ester reductases. Appl Microbiol Biotechnol 38 (1992) 334-340
66. Peters J., Minuth T., and Kula M.R. A novel NADH-dependent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization. Enzyme Microb Technol 15 (1993) 950-958
67. Petschacher B., and Nidetzky B. Altering the coenzyme preference of xylose reductase to favor utilization of NADH enhances ethanol yield from xylose in a metabolically engineered strain of Saccharomyces cerevisiae. Microb Cell Fact 7 (2008)
68. Prelog V. Specification of the stereospecificity of some oxidoreductases by diamond lattice sections. Pure Appl Chem 9 (1964) 119-130
69. Ran N., Zhao L., Chen Z., and Tao J. Recent applications of biocatalysis in developing green chemistry for chemical synthesis at the industrial scale. Green Chem 10 (2008) 361-372
70. Reetz M.T. Controlling the enantioselectivity of enzymes by directed evolution: practical and theoretical ramifications. Proc Nat Acad Sci 101 (2004) 5716-5722
71. Ruinatscha R., Höllrigl V., Otto K., and Schmid A. Productivity of selective electroenzymatic reduction and oxidation reactions: theoretical and practical considerations. Adv Synth Catal 348 (2006) 2015-2026
72. Schubert T., Hummel W., Kula M.R., and Müller M. Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases. Eur J Org Chem 2001 (2001) 4181-4187
73. Schütte H., Fossdorf J., Sahm H., and Kula M.R. Purification and properties of formaldehyde dehydrogenase and formate dehydrogenase from Candida boidinii. Eur J Biochem 62 (1976) 151-160
74. Shimizu S., Hata H., and Yamada H. Reduction of ketopantoyl lactone to D-(-)-pantoyl lactone by microorganisms. Agric Biol Chem 48 (1984) 2285-2291
75. Slusarczyk H., Felber S., Kula M.R., and Pohl M. Stabilization of NAD-dependent formate dehydrogenase from Candida boidinii by site-directed mutagenesis of cysteine residues. Eur J Biochem 267 (2000) 1280-1289
76. Soni P., and Banerjee U.C. Biotransformations for the production of the chiral drug (S)-duloxetine catalyzed by a novel isolate of Candida tropicalis. Appl Microbiol Biotechnol 67 (2005) 771-777
77. Soni P., and Banerjee U.C. Enantioselective reduction of acetophenone and its derivatives with a new yeast isolate Candida tropicalis PBR-2 MTCC 5158. Biotech J 1 (2006) 80-85
78. Soni P., Prasad G., and Banerjee U. Optimization of physicochemical parameters for the enhancement of carbonyl reductase production by Candida viswanathii. Bioproc Biosystem Eng 29 (2006) 149-156
79. Soni P., Kansal H., and Banerjee U.C. Purification and characterization of an enantioselective carbonyl reductase from Candida viswanathii MTCC 5158. Proc Biochem 42 (2007) 1632-1640
80. Steinreiber J., Faber K., and Griengl H. De-racemization of enantiomers versus de-epimerization of diastereomers. Classification of dynamic kinetic asymmetric transformations (DYKAT). Chem Eur J. 14 (2008) 8060-8072
81. Tao J., Zhao D., and Ran N. Recent advances in developing chemoenzymatic processes for active pharmaceutical ingredients. Org Process Res Dev 11 (2007) 259-267
82. Titu D., and Chadha A. Enantiomerically pure allylic alcohols: preparation by Candida parapsilosis ATCC 7330 mediated deracemisation. Tetrahedron: Asymmetry 19 (2008) 1698-1701
83. Titu D., and Chadha A. Preparation of optically pure alkyl 3-(hetero-2-yl)-3- hydroxypropanoates by Candida parapsilosis ATCC 7330 mediated deracemisation. J Mol Catal B: Enz. 52-53 (2008) 168-172
84. Torres Pazmiño D.E., Snajdrova R., Baas B.J., Ghobrial M., Mihovilovic M.D., and Fraaije M.W. Self-sufficient Baeyer-Villiger monooxygenases: effective coenzyme regeneration for biooxygenation by fusion engineering. Angew Chem Int Ed 47 (2008) 2275-2278
85. Vaijayanthi T., and Chadha A. Preparation of enantiomerically pure (3E)-alkyl-4-(hetero-2-yl)-2-hydroxybut-3-enoates by Candida parapsilosis ATCC 7330 mediated deracemisation and determination of the absolute configuration of (3E)-ethyl-4-(thiophene-2-yl)-2-hydroxybut-3-enoate. Tetrahedron: Asymmetry 18 (2007) 1077-1084
86. Vaijayanthi T., and Chadha A. Preparation of optically pure (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates by Candida parapsilosis ATCC 7330 mediated deracemisation of the racemates. Tetrahedron 63 (2007) 4126-4133
87. Vaijayanthi T., and Chadha A. Asymmetric reduction of aryl imines using Candida parapsilosis ATCC 7330. Tetrahedron: Asymmetry 19 (2008) 93-96
88. Voss C.V., Gruber C.C., and Kroutil W. Deracemization of secondary alcohols through a concurrent tandem biocatalytic oxidation and reduction. Angew Chem Int Ed 47 (2008) 741-745
89. Xie Q., Wu J., Xu G., and Yang L. Asymmetric reduction of o-chloroacetophenone with Candida pseudotropicalis 104. Biotechnol Prog 22 (2006) 1301-1304
90. Yamamoto H., Matsuyama A., and Kobayashi Y. Synthesis of ethyl (R)-4-chloro-3-hydroxybutanoate with recombinant Escherichia coli cells expressing (S)-specific secondary alcohol dehydrogenase. Biosci Biotechnol Biochem 66 (2002) 481-483
91. Zelinski T., Liese A., Wandrey C., and Kula M.R. Asymmetric reductions in aqueous media: enzymatic synthesis in cyclodextrin containing buffers. Tetrahedron: Asymmetry 10 (1999) 1681-1687
92. Zhu D., Yang Y., and Hua L. Stereoselective enzymatic synthesis of chiral alcohols with the use of a carbonyl reductase from Candida magnoliae with anti-Prelog enantioselectivity. J Org Chem 71 (2006) 4202-4205