Utilizing the Trispyrazolyl Borate Ligand for the Mimicking of O2-Activating Mononuclear Nonheme Iron Enzymes

Accounts of Chemical Research

Volumn 48, Issue 10, 2015, Pages 2734-2743

  Sallmann, Madleen ^a   Limberg, Christian ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL ACETONE DIOXYGENASE, ACINETOBACTER JOHNSONII; BORIC ACID; CYSTEINE DIOXYGENASE; DIOXYGENASE; LIGAND; PYRAZOLE DERIVATIVE;

BIOMIMETICS; CHEMISTRY; METABOLISM;

BIOMIMETICS; BORATES; CYSTEINE DIOXYGENASE; DIOXYGENASES; LIGANDS; PYRAZOLES;

EID: 84945924815     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00148     Document Type: Article

References (42)

1. Trofimenko, S. Scorpionates; Imperial College Press: London, 1999.
2. Armstrong, W. H.; Lippard, S. J. J. Am. Chem. Soc. 1983, 105, 4837-4838 10.1021/ja00352a053
3. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Dioxygen Activation at Mononuclear Nonheme Iron Active Sites: Enzymes, Models, and Intermediates Chem. Rev. 2004, 104, 939-986 10.1021/cr020628n
4. See Burzlaff, N. Biomimetic Trispyrazolylborato Iron Complexes Angew. Chem., Int. Ed. 2009, 48, 5580-5582 and references therein. 10.1002/anie.200900552
5. Oddon, F.; Chiba, Y.; Nakazawa, J.; Ohta, T.; Ogura, T.; Hikichi, S. Characterization of Mononuclear Non-heme Iron(III)-Superoxo Complex with a Five-Azole Ligand Set Angew. Chem., Int. Ed. 2015, 54, 7336-7339 10.1002/anie.201502367
6. References cited in ref 5a.
7. Joseph, C. A.; Maroney, M. J. Cysteine dioxygenase: structure and mechanism Chem. Commun. 2007, 3338-3349 10.1039/b702158e
8. Buongiorno, D.; Straganz, G. D. Structure and function of atypically coordinated enzymatic mononuclear non-heme-Fe(II) centers Coord. Chem. Rev. 2013, 257, 541-563 10.1016/j.ccr.2012.04.028
9. Straganz, G. D.; Glieder, A.; Brecker, L.; Ribbons, D. W.; Steiner, W. Acetylacetone-cleaving enzyme Dke1: a novel C-C-bond-cleaving enzyme from Acinetobacter johnsonii Biochem. J. 2003, 369, 573-581 10.1042/bj20021047
10. Simmons, C. R.; Liu, Q.; Huang, Q.; Hao, Q.; Begley, T. P.; Karplus, P. A.; Stipanuk, M. H. Crystal Structure of Mammalian Cysteine Dioxygenase: A NOVEL MONONUCLEAR IRON CENTER FOR CYSTEINE THIOL OXIDATION J. Biol. Chem. 2006, 281, 18723-18733 10.1074/jbc.M601555200
11. Ye, S.; Wu, X.; Wei, L.; Tang, D.; Sun, P.; Bartlam, M.; Rao, Z. An Insight into the Mechanism of Human Cysteine Dioxygenase: KEY ROLES OF THE THIOETHER-BONDED TYROSINE-CYSTEINE COFACTOR J. Biol. Chem. 2007, 282, 3391-3402 10.1074/jbc.M609337200
12. Aluri, S.; de Visser, S. P. The Mechanism of Cysteine Oxygenation by Cysteine Dioxygenase Enzymes J. Am. Chem. Soc. 2007, 129, 14846-14847 10.1021/ja0758178
13. 2+-Bound Persulfenate Intermediate in Cysteine Dioxygenase Biochemistry 2008, 47, 11390-11392 10.1021/bi801546n
14. Kumar, D.; Thiel, W.; de Visser, S. P. Theoretical Study on the Mechanism of the Oxygen Activation Process in Cysteine Dioxygenase Enzymes J. Am. Chem. Soc. 2011, 133, 3869-3882 10.1021/ja107514f
15. Souness, R. J.; Kleffmann, T.; Tchesnokov, E. P.; Wilbanks, S. M.; Jameson, G. B.; Jameson, G. N. L. Mechanistic Implications of Persulfenate and Persulfide Binding in the Active Site of Cysteine Dioxygenase Biochemistry 2013, 52, 7606-7617 10.1021/bi400661a
16. McQuilken, A. D.; Goldberg, D. P. Sulfur oxygenation in biomimetic non-heme iron-thiolate complexes Dalton Trans. 2012, 41, 10883-10899 also compare references in refs 16-18. 10.1039/c2dt30806a
17. 2: Synthetic Models of Cysteine Dioxygenase J. Am. Chem. Soc. 2010, 132, 12214-12215 10.1021/ja105591q
18. 2 Activation by Bis(imino)pyridine Iron(II)-Thiolate Complexes J. Am. Chem. Soc. 2011, 133, 1274-1277 10.1021/ja109923a
19. McDonald, A. R.; Bukowski, M. R.; Farquhar, E. R.; Jackson, T. A.; Koehntop, K. D.; Sook Seo, M.; De Hont, R. F.; Stubna, A.; Halfen, J. A.; Münck, E.; Nam, W.; Que, L., Jr. Sulfur versus Iron Oxidation in an Iron-Thiolate Model Complex J. Am. Chem. Soc. 2010, 132, 17118-17129 10.1021/ja1045428
20. Tietz, T.; Limberg, C.; Stößer, R.; Ziemer, B. Four-Coordinate Trispyrazolylboratomanganese and -iron Complexes with a Pyrazolato Co-ligand: Syntheses and Properties as Oxidation Catalysts Chem.-Eur. J. 2011, 17, 10010-10020 10.1002/chem.201100343
21. Sallmann, M.; Siewert, I.; Fohlmeister, L.; Limberg, C.; Knispel, C. A Trispyrazolylborato Iron Cysteinato Complex as a Functional Model for the Cysteine Dioxygenase Angew. Chem., Int. Ed. 2012, 51, 2234-2237 10.1002/anie.201107345
22. Sallmann, M.; Kumar, S.; Chernev, P.; Nehrkorn, J.; Schnegg, A.; Kumar, D.; Dau, H.; Limberg, C.; de Visser, S. P. Structure and mechanism leading to formation of the cysteine sulfinate product complex of a biomimetic cysteine dioxygenase model Chem.-Eur. J. 2015, 21, 7470-7479 10.1002/chem.201500644
23. Alberto, M. E. A trispyrazolylborato iron cysteinato complex efficiently mimics the cysteine dioxygenation process: mechanistic insights Chem. Commun. 2015, 51, 8369-8372 10.1039/C5CC00813A
24. 4S(thiolate) Iron(II) Cysteine Dioxygenase Model Gives a Structurally Characterized Sulfinato-Iron(II) Complex J. Am. Chem. Soc. 2012, 134, 8758-8761 10.1021/ja302112y
25. Dominy, J. E., Jr.; Simmons, C. R.; Hirschberger, L. L.; Hwang, J.; Coloso, R. M.; Stipanuk, M. H. Discovery and Characterization of a Second Mammalian Thiol Dioxygenase, Cysteamine Dioxygenase J. Biol. Chem. 2007, 282, 25189-25198 10.1074/jbc.M703089200
26. Beyond that two bacterial homologues of CDO were identified, which catalyze the oxidation of 3-mercaptopropionate: Bruland, N.; Wübbeler, J. H.; Steinbuchel, A. 3-Mercaptopropionate dioxygenase, a cysteine dioxygenase homologue, catalyzes the initial step of 3-mercaptopropionate catabolism in the 3,3′-thiodipropionic acid degrading bacterium Variovorax paradoxus A J. Biol. Chem. 2009, 284, 660-672 10.1074/jbc.M806762200
27. Sallmann, M.; Limberg, C.; Braun, B. Dioxygenation of cysteamine to hypotaurine at a tris(pyrazolyl)borate iron(II) unit-cysteamine dioxygenase mimicking? Chem. Commun. 2015, 51, 6785-6787 10.1039/C5CC01083G
28. Allpress, C. J.; Berreau, L. M. Oxidative aliphatic carbon-carbon bond cleavage reactions Coord. Chem. Rev. 2013, 257, 3005-3029 10.1016/j.ccr.2013.06.001
29. Straganz, G.; Brecker, L.; Weber, H.-J.; Steiner, W.; Ribbons, D. W. A novel β-diketone-cleaving enzyme from Acinetobacter johnsonii: acetylacetone 2,3-oxygenase Biochem. Biophys. Res. Commun. 2002, 297, 232-236 10.1016/S0006-291X(02)02182-4
30. Hong, S.; Sutherlin, K. D.; Park, J.; Kwon, E.; Siegler, M. A.; Solomon, E. I.; Nam, W. Nat. Commun. 2014, 5, 5440-5447 10.1038/ncomms6440
31. 2+-Dependent β-Diketone Dioxygenase and Their Mechanistic Implications J. Am. Chem. Soc. 2004, 126, 12202-12203 10.1021/ja0460918
32. 2+-Dependent Dioxygenase Dke1 J. Am. Chem. Soc. 2005, 127, 12306-12314 10.1021/ja042313q
33. Diebold, A. R.; Straganz, G. D.; Solomon, E. I. Spectroscopic and Computational Studies of α-Keto Acid Binding to Dke1: Understanding the Role of the Facial Triad and the Reactivity of β-Diketones J. Am. Chem. Soc. 2011, 133, 15979-15991 10.1021/ja203005j
34. Siewert, I.; Limberg, C. A Trispyrazolylborato Iron Malonato Complex as a Functional Model for the Acetylacetone Dioxygenase Angew. Chem., Int. Ed. 2008, 47, 7953-7956 10.1002/anie.200802955
35. Kitajima, N.; Amagai, H.; Tamura, N.; Ito, M.; Moro-oka, Y.; Heerwegh, K.; Pénicaud, A.; Mathur, R.; Reed, C. A.; Boyd, P. D. W. Novel formation of a linear trinuclear ferric complex containing a μ-Oxo Bis(μ-acetato) and a μ-Hydroxo Bis(μ-acetato) Bridge Inorg. Chem. 1993, 32, 3583-3584 10.1021/ic00069a004
36. Siewert, I.; Limberg, C.; Demeshko, S.; Hoppe, E. A Dinuclear Iron Complex Based on Parallel Malonate Binding Sites: Cooperative Activation of Dioxygen and Biomimetic Ligand Oxidation Chem.-Eur. J. 2008, 14, 9377-9388 10.1002/chem.200800955
37. Siewert, I.; Limberg, C. Low-Molecular Weight Analogues of the Soluble Methane Monooxygenase: From the Structural Mimicking of Resting-States and Intermediates to Functional Models Chem.-Eur. J. 2009, 15, 10316-10328 10.1002/chem.200901910
38. Park, H.; Baus, J. S.; Lindeman, S. V.; Fiedler, A. T. Synthesis and Characterization of Fe(II) β-Diketonato Complexes with Relevance to Acetylacetone Dioxygenase: Insights into the Electronic Properties of the 3-Histidine Facial Triad Inorg. Chem. 2011, 50, 11978-11989 10.1021/ic201115s
39. Diebold, A. R.; Neidig, M. L.; Moran, G. R.; Straganz, G. D.; Solomon, E. I. The Three-His Triad in Dke1: Comparisons to the Classical Facial Triad Biochemistry 2010, 49, 6945-6952 10.1021/bi100892w
40. 2 and NO Reactivity Inorg. Chem. 2012, 51, 10279-10289 10.1021/ic3012712
41. Zhang, Z.; Ren, J.-S.; Clifton, I. J.; Schofield, C. J. Crystal Structure and Mechanistic Implications of 1-Aminocyclopropane-1-Carboxylic Acid Oxidase-The Ethylene-Forming Enzyme Chem. Biol. 2004, 11, 1383-1394 10.1016/j.chembiol.2004.08.012
42. Sallmann, M.; Oldenburg, F.; Braun, B.; Reglier, M.; Simaan, J.; Limberg, C. A structural and functional model for the 1-aminocyclopropane-1-carboxylic acid oxidase Angew. Chem., Int. Ed. 2015, 10.1002/anie.201502529