New emerging bio-catalysts design in biotransformations

Biotechnology Advances

Volumn 33, Issue 5, 2015, Pages 605-613

  Palomo, Jose M ^a   Filice, Marco ^a  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

Author keywords

Artificial metalloenzymes; Bionanohybrids; Biotransformations; C C bond reaction; Deacetylation; Regioselectivity; Semisynthetic enzymes

Indexed keywords

ACETYLATION; CATALYST ACTIVITY; CHEMICAL MODIFICATION; COMPUTATIONAL CHEMISTRY; ORGANOMETALLICS; REGIOSELECTIVITY;

ARTIFICIAL METALLOENZYMES; BIONANOHYBRIDS; BIOTRANSFORMATIONS; C-C BONDS; DEACETYLATION;

ENZYMES;

BIOTRANSFORMATION; CATALYST; DRUG; ENZYME; ENZYME ACTIVITY; LITERATURE REVIEW; MEDICINE;

ENZYME;

BIOCATALYSIS; BIOTECHNOLOGY; BIOTRANSFORMATION; CHEMISTRY; METABOLISM; PROTEIN ENGINEERING; STEREOISOMERISM;

BIOCATALYSIS; BIOTECHNOLOGY; BIOTRANSFORMATION; ENZYMES; PROTEIN ENGINEERING; STEREOISOMERISM;

EID: 84931004174     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2014.12.010     Document Type: Review

References (83)

1. Blomberg R., Kries H., Pinkas D.M., Mittl P.R., Grütter M.G., Privett H.K., et al. Precision is essential for efficient catalysis in an evolved Kemp eliminase. Nature 2013, 503:418-421.
2. Bornscheuer U.T., Huisman G.W., Kazlauskas R.J., Lutz S., Moore J.C., Robins K. Engineering the third wave of biocatalysis. Nature 2012, 484:185-194.
3. Bos J., Roelfes G. Artificial metalloenzymes for enantioselective catalysis. Curr Opin Chem Biol 2014, 19:135-143.
4. Brabcova J., Filice M., Gutarra M., Palomo J.M. Synthesis of enantiopure drugs and drug intermediates by immobilized lipase-catalysis. Curr Bioact Compd 2013, 9:113-136.
5. Brunsveld L., Kuhlmann J., Alexandrov K., Wittinghofer A., Goody R., Waldmann H. Lipidated ras and rab peptides and proteins - Synthesis, structure, and function. Angew Chem Int Ed 2006, 45:6622-6646.
6. Burton S. Oxidizing enzymes as biocatalysts. Trends Biotechnol 2003, 21:543-549.
7. Cabrera Z., Palomo J.M. Enzymatic desymmetrization of prochiral molecules. Curr Org Synth 2012, 9:791-805.
8. Calvaresia E.C., Hergenrother P.J. Glucose conjugation for the specific targeting and treatment of cancer. Chem Sci 2013, 4:2319-2333.
9. Chalker J.M., Bernardes G.J.L., Lin Y.A., Davis B.G. Chemical modification of proteins at cysteine: opportunities in chemistry and biology. Chem Asian J 2009, 4:630-640.
10. Del Campo N., Chamberlain S.R., Sahakian B.J., Robbins T.W. Biol Psychiatry 2011, 69:145-157.
11. Díaz-Rodríguez A., Davis B.G. Chemical modification in the creation of novel biocatalysts. Curr Opin Chem Biol 2011, 15:211-219.
12. Dicosimo R., McAuliffe J., Poulose A.J., Bohlmann G. Industrial use of immobilized enzymes. Chem Soc Rev 2013, 42:6437-6474.
13. Drauz K., Groger H., May O. Enzyme catalysis in organic synthesis 2012, Wiley-VCH, New York.
14. Durrenberger M., Ward T.R. Recent achievments in the design and engineering of artificial metalloenzymes. Curr Opin Chem Biol 2014, 19:99-106.
15. Eiben C.B., Siegel J.B., Bale J.B., Cooper S., Khatib F., Shen B.W., et al. Increased Diels-Alderase activity through backbone remodeling guided by Foldit players. Nat Biotechnol 2012, 30:190-192.
16. Engström K., Johnston E.V., Verho O., Gustafson K.P., Shakeri M., Tai C.W., et al. Co-immobilization of an enzyme and a metal into the compartments of mesoporous silica for cooperative tandem catalysis: an artificial metalloenzyme. Angew Chem Int Ed 2013, 52:14006-14010.
17. Esté J.A., Cihlar T. Current status and challenges of antiretroviral research and therapy. Antiviral Res 2010, 85:25-33.
18. Faber K. Biotransformation in organic chemistry 2011, Springer-Verlag, Berlin.
19. Filice M., Palomo J.M. Cascade reactions catalyzed by bionanostructures. ACS Catal 2014, 4:1588-1598.
20. Filice M., Romero O., Guisan J.M., Palomo J.M. Trans, trans-2,4-hexadiene incorporation on enzymes for site-specific immobilization and fluorescent labeling. Org Biomol Chem 2011, 9:5535-5540.
21. Filice M., Marciello M., Morales M.D.P., Palomo J.M. Synthesis of heterogeneous enzyme-metal nanoparticle biohybrids in aqueous media and their applications in C-C bond formation and tandem catalysis. Chem Commun 2013, 49:6876-6878.
22. Fujieda N., Yakiyama A., Itoh S. Catalytic oxygenation of phenols by arthropod hemocyanin, an oxygen carrier protein, from Portunus trituberculatus. Dalton Trans 2010, 39:3083-3092.
23. Fujieda N., Hasegawa A., Ishihama K.-I., Itoh S. Artificial dicopper oxidase: rational reprogramming of bacterial metallob-lactamase into a catechol oxidase. Chem Asian J 2012, 7:1203-1207.
24. Gates B.C. Supported gold catalysts: new properties offered by nanometer and sub-nanometer structures. Chem Commun 2013, 49:7876-7877.
25. Genz M., Kçhler V., Krauss M., Singer D., Hoffmann R., Ward T.R., et al. An artificial imine reductase based on the Ribonuclease S scaffold. ChemCatChem 2014, 6:736-740.
26. Giger L., Caner S., Obexer R., Kast P., Baker D., Ban N., et al. Evolution of a designed retro-aldolase leads to complete active site remodeling. Nat Chem Biol 2013, 9:494-498.
27. Godoy C.A., de las Rivas B., Filice M., Fernández-Lorente G., Guisan J.M., Palomo J.M. Enhanced activity of an immobilized lipase promoted by site-directed chemical modification with polymers. Process Biochem 2010, 45:534-541.
28. Gutarra M.L., Romero O., Abian O., Torres F.A.G., Freire D.M.G., Castro A.M., et al. Enzyme surface glycosylation on the solid phase: improve activity and selectivity of Candida antarctica lipase B. ChemCatChem 2011, 3:1902-1910.
29. Hackenberger C.P.R., Schwarzer D. Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed 2008, 47:10030-10074.
30. Hilvert D. Design of protein catalysts. Annu Rev Biochem 2013, 82:447-470.
31. Hyster T.K., Knörr L., Ward T.R., Rovis T. Biotinylated Rh(III) complexes in engineered streptavidin for accelerated asymmetric C-H activation. Science 2012, 338:500-503.
32. Johansson -Seechurn C.C., Kitching M.O., Colacot T.J., Snieckus V. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize. Angew Chem Int Ed Engl 2012, 1:5062-5085.
33. Kanbak-Aksu S., Nahid Hasan M., Hagen W.R., Hollmann F., Sordi D., Sheldon R.A., et al. Ferritin-supported palladium nanoclusters: selective catalysts for aerobic oxidations in water. Chem Commun 2012, 48:5745-5747.
34. Kelly W.L. Intramolecular cyclizations of polyketide biosynthesis: mining for a "Diels-Alderase"?. Org Biomol Chem 2008, 6:4483-4493.
35. Kim R.R., Illarionov B., Joshi M., Cushman M., Lee C.Y., Eisenreich W., et al. Mechanistic insights on riboflavin synthase inspired by selective binding of the 6,7-dimethyl-8-ribityllumazine exomethylene anion. J Am Chem Soc 2010, 132:2983-2990.
36. Kim H.J., Ruszczycky M.W., Choi S.-H., Liu Y., Liu H.-w. Nature 2011, 473:109-112.
37. Kiss G., Çelebi-Ölçüm N., Moretti R., Baker D., Houk K.N. Computational enzyme design. Angew Chem Int Ed Engl 2013, 52:5700-5725.
38. Kohler V., Wilson Y.M., Durrenberger M., Ghislieri D., Churakova E., Quinto T., et al. Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes. Nat Chem 2013, 5:93-99.
39. Lewis J.C. ACS Catal 2013, 3:2954-2975.
40. Liang T.J., Ghany M.G. Current and future therapies for hepatitis C virus infection. N Engl J Med 2013, 368:1907-1917.
41. 2 nanoparticles as both peroxidase and oxidase mimics. Analyst 2012, 137:4552-4558.
42. Liu W., Huang X., Cheng M.-J., Nielsen R.-J., Goddard W.A., Groves J. Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin. Science 2012, 337:1322-1325.
43. Lo C., Ringenberg M.R., Gnandt D., Wilson Y., Ward T.R. Artificial metalloenzymes for olefin metathesis based on the biotin-(strept)avidin technology. Chem Commun 2011, 47:12065-12067.
44. Ma S.A., Li J., Choi J.W., Zhou H., Lee M., Moorthie V., et al. Complete reconstitution of a highly-reducing iterative polyketide synthase. Science 2009, 326:589-592.
45. Marciello M., Filice M., Palomo J.M. Different strategies to enhance activities of lipase catalysts. Catal Sci Technol 2012, 2:1531-1543.
46. Mateo C., Palomo J.M., Fernández-Lorente G., Fernandez-Lafuente R., Guisan J.M. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb Technol 2007, 40:1451-1463.
47. Matsuo T., Fukumoto K., Watanabe T., Hayashi T. Precise design of artificial cofactors for enhancing peroxidase activity of myoglobin: myoglobin mutant H64D reconstituted with a "single-winged cofactor" is equivalent to native horseradish peroxidase in oxidation activity. Chem Asian J 2011, 6:2491-2499.
48. Matsuo T., Imai C., Yoshida T., Saito T., Hayashi T., Hirota S. Creation of an artificial metalloprotein with a Hoveyda-Grubbs catalyst moiety through the intrinsic inhibition mechanism of a-chymotrypsin. Chem Commun 2012, 48:1662-1664.
49. Mayer C., Gillingham D.G., Ward T.R., Hilvert D. An artificial metalloenzyme for olefin metathesis. Chem Commun 2011, 47:12068-12070.
50. Monnard F.W., Nogueira E.S., Heinisch T., Schirmer T., Ward T.R. Human carbonic anhydrase II as host protein for the creation of artificial metalloenzymes: the asymmetric transfer hydrogenation of imines. Chem Sci 2013, 4:3269-3274.
51. Muller M. Recent developments in enzymatic asymmetric C-C bond formation. Adv Synth Catal 2012, 354:3161-3174.
52. Muralidharan V., Muir T.W. Protein ligation: an enabling technology for the biophysical analysis of proteins. Nat Methods 2006, 3:429-438.
53. Okun Z., Gross Z. Fine tuning the reactivity of corrole-based catalytic antioxidants. Inorg Chem 2012, 51:8083-8090.
54. Oohora K., Kihira Y., Mizohata E., Inoue T., Hayash T. C(sp3)-H bond hydroxylation catalyzed by myoglobin reconstituted with manganese porphycene. J Am Chem Soc 2013, 135:17282-17285.
55. Palomo J.M. Lipases enantioselectivity alteration by immobilization techniques. Curr Bioact Compd 2008, 4:126-138.
56. Palomo J.M. Modulation of enzymes selectivity via immobilization. Curr Org Synth 2009, 6:1-14.
57. Palomo J.M. Diels-Alder cycloaddition in protein chemistry. Eur J Org Chem 2010, 33:6303-6314.
58. Palomo J.M. Click reactions in protein chemistry: from the preparation of semisynthetic enzymes to new click enzymes. Org Biomol Chem 2012, 10:9309-9318.
59. Palomo J.M. Solid-phase peptide synthesis: an overview focused on the preparation of biologically relevant peptides. RSC Adv 2014, 4:32658-32672.
60. Palomo J.M., Lumbierres M., Waldmann H. Efficient Solid-phase synthesis of lipopeptides employing the Ellman sulfonamide linker. Angew Chem Int Ed 2006, 45:477-481.
61. Philippart F., Arlt M., Gotzen S., Tenne S.-J., Bocola M., Chen H.-H., et al. A hybrid ring-opening metathesis polymerization catalyst based on an engineered variant of the b-barrel protein FhuA. Chem Eur J 2013, 19:13865-13871.
62. Pordea A., Creus M., Panek J., Duboc C., Mathis D., Novic M., et al. Artificial metalloenzyme for enantioselective sulfoxidation based on vanadyl-loaded streptavidin. J Am Chem Soc 2008, 130:8085-8088.
63. Preiswerka N., Becka T., Schulza J.D., Milovníka P., Mayera C., Siegel J.B., et al. Impact of scaffold rigidity on the design and evolution of an artificial Diels-Alderase. Proc Natl Acad Sci (PNAS) 2014, 111:8013-8018.
64. Reetz M.T. Artificial metalloenzymes as catalysts in stereoselective Diels-Alder reactions. Chem Rec 2012, 12:391-406.
65. Romero O., Filice M., de las Rivas B., Carrasco-Lopez C., Klett J., Morreale A., et al. Semisynthetic peptide-lipase conjugates for improved biotransformations. Chem Commun 2012, 72:9053-9055.
66. Romero O., Rivero C.W., Guisan J.M., Palomo J.M. Novel enzyme-polymer conjugates for biotechnological applications. PeerJ 2013, e27.
67. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., Witholt B. Industrial biocatalysis today and tomorrow. Nature 2001, 409:258-268.
68. Sheldon R.A. Enzyme immobilization: the quest for optimum performance. Adv Synth Catal 2007, 349:1289-1307.
69. Siegel J.B., Zanghellini A., Lovick H.M., Kiss G., Lambert A.R., St.Clair J.L., et al. Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction. Science 2010, 329:309-313.
70. Simana P., Ashraf B. Chemical and semisynthesis of posttranslationally modified proteins. Org Biomol Chem 2012, 10:5684-5697.
71. Sletten E.M., Bertozzi C.R. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 2009, 48:6974-6998.
72. Srour H., Maux P.L., Simonneaux G. Enantioselective manganese-porphyrin-catalyzed epoxidation and C-H hydroxylation with hydrogen peroxide in water/methanol solutions. Inorg Chem 2012, 51:5850-5856.
73. Steinkellner G., Gruber C.C., Pavkov-Keller T., Binter A., Steiner K., Winkler C., et al. Identification of promiscuous ene-reductase activity by mining structural databases using active site constellations. Nat Commun 2014, 5:4150.
74. Stocking E.M., Williams R.M. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew Chem Int Ed 2003, 42:3078-3115.
75. Straathof A.J.J., Panke S., Schmid A. The production of fine chemicals by biotransformations. Curr Opin Biotechnol 2002, 13:548-556.
76. Turner N.J. Directed evolution drives the next generation of biocatalysts. Nat Chem Biol 2009, 5:567-573.
77. Ueno T., Watanabe Y. Coordination chemistry in protein cages-principles, design, and applications 2013, Wiley-VCH, Weinheim.
78. Ueno T., Abe S., Yokoi N., Watanabe Y. Coordination design of artificial metalloproteins utilizing protein vacant space. Coord Chem Rev 2007, 251:2717-2731.
79. Verger R. 'Interfacial activation' of lipases: facts and artifacts. Trends Biotechnol 1997, 15:32-38.
80. Woodley J.M. Protein engineering of enzymes for process applications. Curr Opin Chem Biol 2013, 17:310-316.
81. Xu W., Yi H., Yuan Y., Jing P., Chai Y., Yuan R., et al. An electrochemical aptasensor for thrombin using synergetic catalysis of enzyme and porous Au@Pd core-shell nanostructures for signal amplification. Biosens Bioelectron 2014, 16:423-428.
82. Yu F., Cangelosi V.M., Zastrow M.L., Tegoni M., Plegaria J.S., Tebo A.G. Protein design: toward functional metalloenzymes. Chem Rev 2014, 114:3495-3578.
83. Zimbron J.M., Heinisch T., Schmid M., Hamels D., Nogueira E.S., Schirmer T., et al. A dual anchoring strategy for the localization and activation of artificial metalloenzymes based on the biotin-streptavidin technology. J Am Chem Soc 2013, 1355:384-388.