Functional models of α-keto acid dependent nonheme iron oxygenases: synthesis and reactivity of biomimetic iron(II) benzoylformate complexes supported by a 2,9-dimethyl-1,10-phenanthroline ligand
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- 作者：Oindrila Das (1)
Sayanti Chatterjee (1)
Tapan Kanti Paine (1) - 关键词：Iron ; Benzoylformate ; O–O activation ; Decarboxylation ; Functional models
- 刊名：Journal of Biological Inorganic Chemistry
- 出版年：2013
- 出版时间：March 2013
- 年：2013
- 卷：18
- 期：3
- 页码：401-410
- 全文大小：409KB
- 参考文献：1. Costas M, Mehn MP, Jensen MP, Que L Jr (2004) Chem Rev 104:939-86 CrossRef
2. Hausinger RP (2004) Crit Rev Biochem Mol Biol 39:21-8 CrossRef
3. Purpero V, Moran GR (2007) J Biol Inorg Chem 12:587-01 CrossRef
4. Hegg EL, Que L Jr (1997) Eur J Biochem 250:625-29 CrossRef
5. Abu-Omar MM, Loaiza A, Hontzeas N (2005) Chem Rev 105:2227-252 CrossRef
6. Que L Jr (2000) Nat Struct Biol 7:182-84 CrossRef
7. Straganz GD, Nidetzky B (2006) ChemBioChem 7:1536-548 CrossRef
8. Koehntop KD, Emerson JP, Que L Jr (2005) J Biol Inorg Chem 10:87-3 CrossRef
9. Elkins JM, Ryle MJ, Clifton IJ, Hotopp JCD, Lloyd JS, Burzlaff NI, Baldwin JE, Hausinger RP, Roach PL (2002) Biochemistry 41:5185-192 CrossRef
10. Price JC, Barr EW, Glass TE, Krebs C, Bollinger JM Jr (2003) J Am Chem Soc 125:13008-3009 CrossRef
11. Krebs C, Fujimori DG, Walsh CT, Bollinger JM Jr (2007) Acc Chem Res 40:484-92 CrossRef
12. Hoffart LM, Barr EW, Guyer RB, Bollinger JM Jr, Krebs C (2006) Proc Natl Acad Sci USA 103:14738-4743 CrossRef
13. Galonic DP, Barr EW, Walsh CT, Bollinger JM Jr, Krebs C (2007) Nat Chem Biol 3:113-16 CrossRef
14. Price JC, Barr EW, Tirupati B, Bollinger JM Jr, Krebs C (2003) Biochemistry 42:7497-508 CrossRef
15. Proshlyakov DA, Henshaw TF, Monterosso GR, Ryle MJ, Hausinger RP (2004) J Am Chem Soc 126:1022-023 CrossRef
16. Sinnecker S, Svensen N, Barr EW, Ye S, Bollinger JM Jr, Neese F, Krebs C (2007) J Am Chem Soc 129:6168-179 CrossRef
17. Price JC, Barr EW, Hoffart LM, Krebs C, Bollinger JM Jr (2005) Biochemistry 44:8138-147 CrossRef
18. Hoffart LM, Barr EW, Guyer RB, Bollinger JM Jr, Krebs C (2006) Proc Natl Acad Sci USA 103:14738-4743 CrossRef
19. Matthews ML, Krest CM, Barr EW, Vaillancourt FH, Walsh CT, Green MT, Krebs C, Bollinger JM Jr (2009) Biochemistry 48:4331-333 CrossRef
20. Galoni? Fujimori D, Barr EW, Matthews ML, Koch GM, Yonce JR, Walsh CT, Bollinger JM Jr, Krebs C, Riggs-Gelasco PJ (2007) J Am Chem Soc 129:13408-3409 CrossRef
21. Riggs-Gelasco PJ, Price JC, Guyer RB, Brehm JH, Barr EW, Bollinger JM Jr, Krebs C (2004) J Am Chem Soc 126:8108-109 CrossRef
22. Bassan A, Borowski T, Siegbahn PEM (2004) Dalton Trans 3153-3162
23. Borowski T, Bassan A, Siegbahn PEM (2004) Chem Eur J 10:1031-041 CrossRef
24. de Visser SP (2007) Chem Commun 171-73
25. Rohde J-U, In JH, Lim MH, Brennessel WW, Bukowski MR, Stubna A, Münck E, Nam W, Que L Jr (2003) Science 299:1037-039 CrossRef
26. Lim MH, Rohde J-U, Stubna A, Bukowski MR, Costas M, Ho RYN, Münck E, Nam W, Que L Jr (2003) Proc Natl Acad Sci USA 100:3665-670 CrossRef
27. England J, Martinho M, Farquhar ER, Frisch JR, Bominaar EL, Münck E, Que L Jr (2009) Angew Chem Int Ed 46:3622-626 CrossRef
28. England J, Guo Y, Farquhar ER, Young VG Jr, Münck E, Que L Jr (2010) J Am Chem Soc 132:8635-644 CrossRef
29. Que L Jr (2007) Acc Chem Res 40:493-00 CrossRef
30. Klinker EJ, Kaizer J, Brennessel WW, Woodrum NL, Cramer CJ, Que L Jr (2005) Angew Chem Int Ed 44:3690-694 CrossRef
31. Kaizer J, Klinker EJ, Oh NY, Rohde J-U, Song WJ, Stubna A, Kim J, Nam W, Münck E, Que L Jr (2004) J Am Chem Soc 126:472-73 CrossRef
32. England J, Guo Y, Van Heuvelen KM, Cranswick MA, Rohde GT, Bominaar EL, Münck E, Que L Jr (2011) J Am Chem Soc 133:11880-1883 CrossRef
33. Chiou Y-M, Que L Jr (1995) J Am Chem Soc 117:3999-013 CrossRef
34. Ha EH, Ho RYN, Kisiel JF, Valentine JS (1995) Inorg Chem 34:2265-266 CrossRef
35. Hikichi S, Ogihara T, Fujisawa K, Kitajima N, Akita M, Moro-oka Y (1997) Inorg Chem 36:4539-547 CrossRef
36. Chiou Y-M, Que L Jr (1994) Angew Chem Int Ed 33:1886-888 CrossRef
37. Hegg EL, Ho RYN, Que L Jr (1999) J Am Chem Soc 121:1972-973 CrossRef
38. Mehn MP, Fujisawa K, Hegg EL, Que L Jr (2003) J Am Chem Soc 125:7828-842 CrossRef
39. Mukherjee A, Martinho M, Bominaar EL, Münck E, Que L Jr (2009) Angew Chem Int Ed 48:1780-783 CrossRef
40. Mukherjee A, Cranswick MA, Chakrabarti M, Paine TK, Fujisawa K, Münck E, Que L Jr (2010) Inorg Chem 49:3618-628 CrossRef
41. Paine TK, Zheng H, Que L Jr (2005) Inorg Chem 44:474-76 CrossRef
42. Paine TK, England J, Que L Jr (2007) Chem Eur J 13:6073-081 CrossRef
43. Parkin G (2004) Chem Rev 104:699-68 CrossRef
44. Bruijnincx PCA, Lutz M, Spek AL, Hagen WR, Weckhuysen BM, van Koten G, Gebbink RJMK (2007) J Am Chem Soc 129:2275-286 CrossRef
45. Bruijnincx PCA, van Koten G, Gebbink RJMK (2008) Chem Soc Rev 37:2716-744 CrossRef
46. Paria S, Halder P, Paine TK (2010) Inorg Chem 49:4518-523 CrossRef
47. Beck A, Weibert B, Burzlaff N (2001) Eur J Inorg Chem 521-27
48. Beck A, Barth A, Hübner E, Burzlaff N (2003) Inorg Chem 42:7182-188 CrossRef
49. Burzlaff N (2008) Adv Inorg Chem 60:101-65 CrossRef
50. Cappillino PJ, Miecznikowski JR, Tyler LA, Tarves PC, McNally JS, Lo W, Kasibhatla BST, Krzyaniak MD, McCracken J, Wang F, Armstrong WH, Caradonna JP (2012) Dalton Trans 41:5662-677 CrossRef
51. Friese SJ, Kucera BE, Que L Jr, Tolman WB (2006) Inorg Chem 45:8003-005 CrossRef
52. Friese SJ, Kucera BE, Young VG Jr, Que L Jr, Tolman WB (2008) Inorg Chem 47:1324-331 CrossRef
53. Dubois G, Murphy A, Stack TDP (2003) Org Lett 5:2469-472 CrossRef
54. Ménage S, Vicent JM, Lambeaux C, Chottard G, Grand A, Fontecave M (1993) Inorg Chem 32:4766-773 CrossRef
55. Ménage S, Vincent JM, Lambeaux C, Fontecave M (1994) J Chem Soc Dalton Trans 2081-084
56. Duboc-Toia C, Menage S, Lambeaux C, Fontecave M (1997) Tetrahedron Lett 38:3727-730 CrossRef
57. Bruker AXS (2006) APEX2, version 2.1-0. Bruker AXS, Madison
58. Farrugia LJ (1999) J Appl Crystallogr 32:837-38 CrossRef
59. Fox DB, Hall JR, Plowman RA (1962) Aust J Chem 15:235-41 CrossRef
60. K?nig E, Ritter G, Madeja K (1981) J Inorg Nucl Chem 43:2273-280 CrossRef
61. Chan BCK, Baird MC (2004) Inorg Chim Acta 357:2776-782 CrossRef
62. Kahn O (1993) Molecular magnetism. VCH, New York
63. Ho RYN, Mehn MP, Hegg EL, Liu A, Ryle MJ, Hausinger RP, Que L Jr (2001) J Am Chem Soc 123:5022-029 CrossRef
64. Shan X, Que L Jr (2005) Proc Natl Acad Sci USA 102:5340-345 CrossRef
65. Maiti D, Lee D-H, Gaoutchenova K, Würtele C, Holthausen MC, Sarjeant AAN, Sundermeyer J, Schindler S, Karlin KD (2008) Angew Chem Int Ed 47:82-5 CrossRef - 作者单位：Oindrila Das (1)
Sayanti Chatterjee (1)
Tapan Kanti Paine (1)
1. Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, 700032, Kolkata, India - ISSN：1432-1327
文摘
Two biomimetic iron(II) benzoylformate complexes, [LFeII(BF)2] (2) and [LFeII(NO3)(BF)] (3) (L is 2,9-dimethyl-1,10-phenanthroline and BF is monoanionic benzoylformate), have been synthesized from an iron(II)–dichloro complex [LFeIICl2] (1). All the iron(II) complexes have been structurally and spectroscopically characterized. The iron(II) center in 2 is coordinated by a bidentate NN ligand (2,9-dimethyl-1,10-phenanthroline) and two monoanionic benzoylformates to form a distorted octahedral coordination geometry. One of the benzoylformates binds to the iron in 2 via both carboxylate oxygens but the other one binds in a chelating bidentate fashion via one carboxylate oxygen and the keto oxygen. On the other hand, the iron(II) center in 3 is ligated by one NN ligand, one bidentate nitrate, and one monoanionic chelating benzoylformate. Both iron(II) benzoylformate complexes exhibit the facial NNO donor environment in their solid-state structures. Complexes 2 and 3 are stable in noncoordinating solvents under an inert atmosphere, but react with dioxygen under ambient conditions to undergo oxidative decarboxylation of benzoylformate to benzoate in high yields. Evidence for the formation of an iron(IV)–oxo intermediate upon oxidative decarboxylation of benzoylformate was obtained by interception and labeling experiments. The iron(II) benzoylformate complexes represent the functional models of α-keto acid dependent oxygenases.