Phenylalanine Ammonia-Lyase-Catalyzed Deamination of an Acyclic Amino Acid: Enzyme Mechanistic Studies Aided by a Novel Microreactor Filled with Magnetic Nanoparticles

ChemBioChem

Volumn 16, Issue 16, 2015, Pages 2283-2288

  Weiser, Diána ^a   Bencze, Lászlõ Csaba ^b   Bánõczi, Gergely ^a   Ender, Ferenc ^a   Kiss, Rõbert ^c   Kõkai, Eszter ^a   Szilágyi, András ^a   Vértessy, Beáta G ^a,d   Farkas, Ödön ^e   Paizs, Csaba ^b   Poppe, Lászlõ ^a,f  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b BABE BOLYAI UNIVERSITY   (Romania)

^c GEDEON RICHTER LTD   (Hungary)

^d INSTITUTE OF ENZYMOLOGY   (Hungary)

^e EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^f SynBiocat Ltd   (Hungary)

Author keywords

enzyme catalysis; magnetic nanoparticles; microreactors; phenylalanine ammonia lyase; reaction mechanisms

Indexed keywords

AMINO ACID; AMMONIA; AROMATIC AMINO ACID; IMIDAZOLE DERIVATIVE; MAGNETIC NANOPARTICLE; PHENYLALANINE AMMONIA LYASE; PROPARGYLGLYCINE; MAGNETITE NANOPARTICLE;

ARTICLE; CATALYSIS; CATALYST; COVALENT BOND; DEAMINATION; ELECTROPHILICITY; ENZYME ACTIVE SITE; ENZYME IMMOBILIZATION; ENZYME MECHANISM; ENZYME SUBSTRATE; FRIEDEL CRAFTS REACTION; MICROFLUIDICS; MOLECULAR MECHANICS; PRIORITY JOURNAL; QUANTUM MECHANICS; REACTION TIME; ULTRAVIOLET DETECTOR; BIOCATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; METABOLISM; MICROFLUIDIC ANALYSIS; QUANTUM THEORY;

AMINO ACIDS; BIOCATALYSIS; DEAMINATION; KINETICS; MAGNETITE NANOPARTICLES; MICROFLUIDIC ANALYTICAL TECHNIQUES; MODELS, MOLECULAR; PHENYLALANINE AMMONIA-LYASE; QUANTUM THEORY;

EID: 84945183335     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201500444     Document Type: Article

References (70)

1. D. S. Hodgins, J. Biol. Chem. 1971, 246, 2977-2985.
2. J. A. Kyndt, T. E. Meyer, M. A. Cusanovich, J. J. Van Beeumen, FEBS Lett. 2002, 512, 240-244.
3. I. L. Givot, T. A. Smith, R. H. Abeles, J. Biol. Chem. 1969, 244, 6341-6353;
4. R. B. Wickner, J. Biol. Chem. 1969, 244, 6550-6552.
5. B. Langer, M. Langer, J. Rétey, Adv. Protein Chem. 2001, 58, 175-214;
6. L. Poppe, J. Rétey, Angew. Chem. Int. Ed. 2005, 44, 3668-3688;
7. Angew. Chem. 2005, 117, 3734-3754.
8. T. F. Schwede, J. Rétey, G. E. Schulz, Biochemistry 1999, 38, 5355-5361.
9. L. Poppe, Curr. Opin. Chem. Biol. 2001, 5, 512-524;
10. J. Rétey, Biochim. Biophys. Acta Proteins Proteomics 2003, 1647, 179-184.
11. J. C. Calabrese, D. B. Jordan, A. Boodhoo, S. Sariaslani, T. Vannelli, Biochemistry 2004, 43, 11403-11416.
12. L. Wang, A. Gamez, C. N. Sarkissian, M. Straub, M. G. Patch, G. W. Han, S. Striepeke, P. Fitzpatrick, C. R. Scriver, R. C. Stevens, Mol. Genet. Metab. 2005, 86, 134-140.
13. H. Ritter, G. E. Schulz, Plant Cell 2004, 16, 3426-3436.
14. M. C. Moffitt, G. V. Louie, M. E. Bowman, J. Pence, J. P. Noel, B. S. Moore, Biochemistry 2007, 46, 1004-1012.
15. L. Wang, A. Gamez, H. Archer, E. E. Abola, C. N. Sarkissian, P. Fitzpatrick, D. Wendt, Y. Zhang, M. Vellard, J. Bliesath, S. M. Bell, J. F. Lemontt, C. R. Scriver, R. C. Stevens, J. Mol. Biol. 2008, 380, 623-635.
16. G. V. Louie, M. E. Bowman, M. C. Moffitt, T. J. Baiga, B. S. Moore, J. P. Noel, Chem. Biol. 2006, 13, 1327-1338.
17. K. D. Walker, K. Klettke, T. Akiyama, R. Croteau, J. Biol. Chem. 2004, 279, 53947-53954;
18. C. L. Steele, Y. Chen, B. A. Dougherty, W. Li, S. Hofstead, K. S. Lam, Z. Xing, S.-J. Chiang, Arch. Biochem. Biophys. 2005, 438, 1-10;
19. W. Mutatu, K. L. Klettke, C. Foster, K. D. Walker, Biochemistry 2007, 46, 9785-9794.
20. L. Feng, U. Wanninayake, S. Strom, J. Geiger, K. D. Walker, Biochemistry 2011, 50, 2919-2930.
21. S. D. Christenson, W. Liu, M. D. Toney, B. Shen, J. Am. Chem. Soc. 2003, 125, 6062-6063;
22. C. V. Christianson, T. J. Montavon, S. G. Van Lanen, B. Shen, S. D. Bruner, Biochemistry 2007, 46, 7205-7214.
23. A. Bélanger-Quintana, A. Burlina, C. O. Harding, A. C. Muntau, Mol. Genet. Metab. 2011, 104, S 19 -S 25.
24. G. Renard, J.-C. Guilleaux, C. Bore, V. Malta-Valette, D. A. Lerner, Biotechnol. Lett. 1992, 14, 673-678;
25. A. Gloge, B. Langer, L. Poppe, J. Rétey, Arch. Biochem. Biophys. 1998, 359, 1-7;
26. L. Poppe, J. Rétey, Curr. Org. Chem. 2003, 7, 1297-1315;
27. C. Paizs, A. Katona, J. Rétey, Chem. Eur. J. 2006, 12, 2739-2744;
28. C. Paizs, A. Katona, J. Rétey, Eur. J. Org. Chem. 2006, 1113-1116;
29. S Bartsch, U. T. Bornscheuer, Angew. Chem. Int. Ed. 2010, 49, 3860-3860;
30. Angew. Chem. 2010, 122, 3951-3951;
31. C. Paizs, I. M. Toşa, C. L. Bencze, J. Brem, F. D. Irimie, J. Rétey, Heterocycles 2010, 82, 1217-1228.
32. H. A. Cooke, C. V. Christianson, S. D. Bruner, Curr. Opin. Chem. Biol. 2009, 13, 460-468.
33. S. Pilbák, Ö. Farkas, L. Poppe, Chem. Eur. J. 2012, 18, 7793-7802.
34. D. Röther, L. Poppe, G. Morlock, S. Viergutz, J. Rétey, Eur. J. Biochem. 2002, 269, 3065-3075.
35. A. C. Schroeder, S. Kumaran, L. M. Hicks, R. E. Cahoon, C. Halls, O. Yu, J. M. Jez, Phytochemistry 2008, 69, 1496-1506.
36. D. Röther, L. Poppe, S. Viergutz, B. Langer, J. Rétey, Eur. J. Biochem. 2001, 268, 6011-6019.
37. S. Pilbak, A. Tomin, J. Rétey, L. Poppe, FEBS J. 2006, 273, 1004-1019.
38. T. A. Smith, F. H. Cordelle, R. H. Abeles, Arch. Biochem. Biophys. 1967, 120, 724-725.
39. M. Langer, A. Pauling, J. Rétey, Angew. Chem. Int. Ed. Engl. 1995, 34, 1464-1465;
40. Angew. Chem. 1995, 107, 1585-1587.
41. K. R. Hanson, E. A. Havir, Arch. Biochem. Biophys. 1970, 141, 1-17.
42. B. Schuster, J. Rétey, Proc. Natl. Acad. Sci. USA 1995, 92, 8433-8437.
43. J. D. Hermes, P. M. Weiss, W. W. Cleland, Biochemistry 1985, 24, 2959-2967.
44. G. P. Pinto, A. J. M. Ribeiro, M. J. Ramos, P. A. Fernandes, M. Toscano, N. Russo, Arch. Biochem. Biophys. 2015, 582, 107-115.
45. R. H. Wightman, J. Staunton, A. R. Battersby, K. R. Hanson, J. Chem. Soc. Perkin Trans. 1 1972, 2355-2364.
46. P. A. Frey, A. D. Hegeman, Enzymatic Reaction Mechanisms, Oxford University Press, New York, 2007, pp. 456-461.
47. A. Skolaut, J. Rétey, Arch. Biochem. Biophys. 2001, 393, 187-191.
48. P. Yager, T. Edwards, E. Fu, K. Helton, K. Nelson, M. R. Tam, B. H. Weigl, Nature 2006, 442, 412-418;
49. M. A. M. Gijs, F. Lacharme, U. Lehmann, Chem. Rev. 2010, 110, 1518-1563;
50. P. N. Nge, C. I. Rogers, A. T. Woolley, Chem. Rev. 2013, 113, 2550-2583;
51. E. K. Sackmann, A. L. Fulton, D. J. Beebe, Nature 2014, 507, 181-189.
52. R. A. Sheldon, Adv. Synth. Catal. 2007, 349, 1289-1307;
53. U. Hanefeld, L. Gardossi, E. Magner, Chem. Soc. Rev. 2009, 38, 453-468;
54. R. A. Sheldon, S. van Pelt, Chem. Soc. Rev. 2013, 42, 6223-6235;
55. R. C. Rodrigues, C. Ortiz, Á. Berenguer-Murcia, R. Torres, R. Fernández-Lafuente, Chem. Soc. Rev. 2013, 42, 6290-6307.
56. S. A. Ansari, Q. Husain, Biotechnol. Adv. 2012, 30, 512-523.
57. J. Xu, J. Sun, Y. Wang, J. Sheng, F. Wang, M. Sun, Molecules 2014, 19, 11465-11486.
58. D. Weiser, A. Varga, K. Kovács, F. Nagy, A. Szilágyi, B. G. Vértessy, C. Paizs, L. Poppe, ChemCatChem 2014, 6, 1463-1469;
59. J. H. Bartha-Vári, M. I. Toşa, F.-D. Irimie, D. Weiser, Z. Boros, B. G. Vértessy, C. Paizs, L. Poppe, ChemCatChem 2015, 7, 1122-1128.
60. N. Pamme, Curr. Opin. Chem. Biol. 2012, 16, 436-443.
61. S. Kurbanoglu, C. C. Mayorga-Martinez, M. Medina-Sánchez, L. Rivas, S. A. Ozkan, A. Merkoçi, Biosens. Bioelectron. 2015, 67, 670-676.
62. K. R. Hanson, E. A. Havir, The Biochemistry of Plants, Vol,. 7 Secondary Plant Products (Eds.:, P. K. Stumpf, E. E. Conn,), Academic Press, New York, 1981, pp. 577-625.
63. J. Rösler, F. Krekel, N. Amrhein, J. Schmid, Plant Physiol. 1997, 113, 175-179.
64. K. T. Watts, B. N. Mijts, P. C. Lee, A. J. Manning, C. Schmidt-Dannert, Chem. Biol. 2006, 13, 1317-1326.
65. T. J. Montavon, C. V. Christianson, G. M. Festin, B. Shen, S. D. Bruner, Bioorg. Med. Chem. Lett. 2008, 18, 3099-3102.
66. H. A. Cooke, S. D. Bruner, Biopolymers 2010, 93, 802-810.
67. G. G. Wybenga, W. Szymanski, B. Wu, B. L. Feringa, D. B. Janssen, B. W. Dijkstra, Biochemistry 2014, 53, 3187-3198.
68. P. G. Strange, J. Staunton, H. R. Wiltshire, A. R. Battersby, K. R. Hanson, E. A. Havir, J. Chem. Soc. Perkin Trans. 1 1972, 18, 2364-2372.
69. S. Yamada, K. Nabe, N. Izuo, K. Nakamichi, I. Chibata, Appl. Environ. Microbiol. 1981, 42, 773-778.
70. J. P. Scannell, D. L. Pruess, T. C. Demny, F. Weiss, T. Williams, A. Stempel, J. Antibiot. 1971, 24, 239-244.