메뉴 건너뛰기




Volumn 36, Issue 7, 2011, Pages 751-759

Iron(III)-salen-H2O2 as a peroxidase model: Electron transfer reactions with anilines

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; AXIAL LIGAND; AZOXYBENZENES; ELECTRON TRANSFER; ELECTRON-TRANSFER REACTIONS; LINEAR RELATIONSHIPS; MICHAELIS-MENTEN KINETIC; REACTION MECHANISM; SALEN COMPLEX;

EID: 80053565763     PISSN: 03404285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11243-011-9529-4     Document Type: Article
Times cited : (26)

References (70)
  • 2
    • 0036197490 scopus 로고    scopus 로고
    • 10.1016/S0010-8545(01)00441-6
    • H Fujji 2002 Coord Chem Rev 226 51 10.1016/S0010-8545(01)00441-6
    • (2002) Coord Chem Rev , vol.226 , pp. 51
    • Fujji, H.1
  • 3
    • 0039302669 scopus 로고    scopus 로고
    • 10.1021/cr960039f 1:CAS:528:DyaK28Xmt1GmsrY%3D
    • L Que Jr RYN Ho 1996 Chem Rev 96 2607 10.1021/cr960039f 1:CAS:528:DyaK28Xmt1GmsrY%3D
    • (1996) Chem Rev , vol.96 , pp. 2607
    • Que Jr., L.1    Ho, R.Y.N.2
  • 4
    • 0343986411 scopus 로고    scopus 로고
    • One motif - Many different reactions
    • DOI 10.1038/73270
    • L Que Jr 2000 Nat Struct Biol 7 182 10.1038/73270 1:CAS:528: DC%2BD3cXhvFSht7o%3D (Pubitemid 30140757)
    • (2000) Nature Structural Biology , vol.7 , Issue.3 , pp. 182-184
    • Que Jr., L.1
  • 7
    • 0030068091 scopus 로고    scopus 로고
    • Role of arginine 38 in horseradish peroxidase. A critical residue for substrate binding and catalysis
    • DOI 10.1074/jbc.271.8.4023
    • JN Rodriguez-Lopez AT Smith RNF Thomley 1996 J Biol Chem 271 4023 10.1074/jbc.271.8.4023 1:CAS:528:DyaK28XhtlSms70%3D (Pubitemid 26070495)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.8 , pp. 4023-4030
    • Rodriguez-Lopez, J.N.1    Smith, A.T.2    Thorneley, R.N.F.3
  • 9
    • 33845278472 scopus 로고
    • 10.1021/ja00233a021 1:CAS:528:DyaL1MXjs1Wg
    • JT Groves Y Watanabe 1988 J Am Chem Soc 110 8443 10.1021/ja00233a021 1:CAS:528:DyaL1MXjs1Wg
    • (1988) J Am Chem Soc , vol.110 , pp. 8443
    • Groves, J.T.1    Watanabe, Y.2
  • 11
    • 0011697055 scopus 로고
    • 10.1021/cr00014a008 1:CAS:528:DyaK38XlslSntLs%3D
    • B Meunier 1992 Chem Rev 92 1411 10.1021/cr00014a008 1:CAS:528: DyaK38XlslSntLs%3D
    • (1992) Chem Rev , vol.92 , pp. 1411
    • Meunier, B.1
  • 12
    • 33751158901 scopus 로고
    • 10.1021/ic00100a035 1:CAS:528:DyaK2cXmsVCitr8%3D
    • JT Groves Z Gross MK Stern 1994 Inorg Chem 33 5065 10.1021/ic00100a035 1:CAS:528:DyaK2cXmsVCitr8%3D
    • (1994) Inorg Chem , vol.33 , pp. 5065
    • Groves, J.T.1    Gross, Z.2    Stern, M.K.3
  • 14
    • 0142183453 scopus 로고    scopus 로고
    • Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD)
    • DOI 10.1021/ja037400h
    • JC Price EW Barr TE Glass C Krebs JM Bollinger 2003 J Am Chem Soc 125 13008 10.1021/ja037400h 1:CAS:528:DC%2BD3sXnslagt7w%3D (Pubitemid 37305581)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.43 , pp. 13008-13009
    • Price, J.C.1    Barr, E.W.2    Glass, T.E.3    Krebs, C.4    Bollinger Jr., J.M.5
  • 15
    • 21844455928 scopus 로고    scopus 로고
    • Reaction mechanisms of mononuclear non-heme iron oxygenases
    • DOI 10.1021/cr040653o
    • MM Abu-Omar A Loaiza N Hontzeas 2005 Chem Rev 105 2227 10.1021/cr040653o 1:CAS:528:DC%2BD2MXivV2lu7s%3D (Pubitemid 40947948)
    • (2005) Chemical Reviews , vol.105 , Issue.6 , pp. 2227-2252
    • Abu-Omar, M.M.1    Loaiza, A.2    Hontzeas, N.3
  • 18
    • 42449157733 scopus 로고
    • Models and mechanism of cytochrome p450 action
    • Ortiz de Montellano PR (ed) 2nd edn. Plenum press, New York
    • Groves JT, Han YZ (1995) Models and mechanism of cytochrome p450 action. In: Ortiz de Montellano PR (ed) Cytochrome P450. Structure, mechanism and biochemistry, 2nd edn. Plenum press, New York, pp 3-48
    • (1995) Cytochrome P450. Structure, Mechanism and Biochemistry , pp. 3-48
    • Groves, J.T.1    Han, Y.Z.2
  • 19
    • 0000239991 scopus 로고    scopus 로고
    • 10.1021/cr9500489 1:CAS:528:DyaK28Xmt1Gnu7c%3D
    • BJ Wallar JD Lipscomb 1996 Chem Rev 96 2625 10.1021/cr9500489 1:CAS:528:DyaK28Xmt1Gnu7c%3D
    • (1996) Chem Rev , vol.96 , pp. 2625
    • Wallar, B.J.1    Lipscomb, J.D.2
  • 20
    • 1542348939 scopus 로고    scopus 로고
    • 10.1021/cr020622y 1:CAS:528:DC%2BD2cXmtFSlsA%3D%3D
    • EY Tshuva SJ Lippard 2004 Chem Rev 104 987 10.1021/cr020622y 1:CAS:528:DC%2BD2cXmtFSlsA%3D%3D
    • (2004) Chem Rev , vol.104 , pp. 987
    • Tshuva, E.Y.1    Lippard, S.J.2
  • 21
    • 21844470744 scopus 로고    scopus 로고
    • Kinetics and mechanisms of formation and reactivity of non-heme iron oxygen intermediates
    • DOI 10.1021/cr030709z
    • SV Kryatov EV Rybak-Akimova S Schindler 2005 Chem Rev 105 2175 10.1021/cr030709z 1:CAS:528:DC%2BD2MXktlKisrY%3D (Pubitemid 40951783)
    • (2005) Chemical Reviews , vol.105 , Issue.6 , pp. 2175-2226
    • Kryatov, S.V.1    Rybak-Akimova, E.V.2    Schindler, S.3
  • 25
    • 0033419296 scopus 로고    scopus 로고
    • 10.1039/a806483k 1:CAS:528:DyaK1MXht12ktLs%3D
    • L Canali DC Sherrington 1999 Chem Soc Rev 28 85 10.1039/a806483k 1:CAS:528:DyaK1MXht12ktLs%3D
    • (1999) Chem Soc Rev , vol.28 , pp. 85
    • Canali, L.1    Sherrington, D.C.2
  • 26
    • 0000775309 scopus 로고
    • 10.1016/0010-8545(94)01124-T 1:CAS:528:DyaK2MXks1Kgsrw%3D
    • T Katsuki 1995 Coord Chem Rev 140 189 10.1016/0010-8545(94)01124-T 1:CAS:528:DyaK2MXks1Kgsrw%3D
    • (1995) Coord Chem Rev , vol.140 , pp. 189
    • Katsuki, T.1
  • 27
    • 0032934747 scopus 로고    scopus 로고
    • Asymmetric catalysis of new generation chiral metallosalen complexes
    • DOI 10.1246/bcsj.72.603
    • YN Ito T Katsuki 1999 Bull Chem Soc Jpn 72 603 10.1246/bcsj.72.603 1:CAS:528:DyaK1MXitlels7g%3D (Pubitemid 29205175)
    • (1999) Bulletin of the Chemical Society of Japan , vol.72 , Issue.4 , pp. 603-619
    • Ito, Y.N.1    Katsuki, T.2
  • 28
    • 0346265937 scopus 로고
    • Wilkinson G, Stone FGA, Abel EW, Hegedus LS, (eds) chap II. Pergamon, New york
    • Jacobsen EN (1995) In: Wilkinson G, Stone FGA, Abel EW, Hegedus LS, (eds) Comprehensive organometallic chemistry II, vol 12, chap II. Pergamon, New york
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Jacobsen, E.N.1
  • 29
    • 20144383282 scopus 로고    scopus 로고
    • Chromium-and manganese-salen promoted epoxidation of alkenes
    • DOI 10.1021/cr0306945
    • EM McGarrigle DG Gilheany 2005 Chem Rev 105 1563 10.1021/cr0306945 1:CAS:528:DC%2BD2MXjt1Oktr8%3D (Pubitemid 40773664)
    • (2005) Chemical Reviews , vol.105 , Issue.5 , pp. 1563-1602
    • McGarrigle, E.M.1    Gilheany, D.G.2
  • 32
    • 0033515659 scopus 로고    scopus 로고
    • Oxidation of aryl methyl sulfoxides by oxo(salen)manganese(V) complexes and the reactivity-selectivity principle
    • DOI 10.1021/jo9815756
    • A Chellamani P Kulandaipandi S Rajagopal 1999 J Org Chem 64 2232 10.1021/jo9815756 1:CAS:528:DyaK1MXhslekt7g%3D (Pubitemid 29180434)
    • (1999) Journal of Organic Chemistry , vol.64 , Issue.7 , pp. 2232-2239
    • Chellamani, A.1    Kulanthaipandi, P.2    Rajagopal, S.3
  • 34
    • 6044234865 scopus 로고    scopus 로고
    • Evidence for the formation of an iodosylbenzene(salen)iron active intermediate in a (salen)iron(III)-catalyzed asymmetric sulfide oxidation
    • DOI 10.1002/anie.200460108
    • KP Bryliakov EP Talsi 2004 Angew Chem Int Ed 43 5228 10.1002/anie. 200460108 1:CAS:528:DC%2BD2cXos1ygs7Y%3D (Pubitemid 39382548)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.39 , pp. 5228-5230
    • Bryliakov, K.P.1    Talsi, E.P.2
  • 35
    • 35048854604 scopus 로고    scopus 로고
    • Iron-catalyzed oxidation of thioethers by iodosylarenes: Stereoselectivity and reaction mechanism
    • DOI 10.1002/chem.200700566
    • KP Bryliakov EP Talsi 2007 Chem Eur J 13 8045 10.1002/chem.200700566 1:CAS:528:DC%2BD2sXhtFOqtLnM (Pubitemid 47556378)
    • (2007) Chemistry - A European Journal , vol.13 , Issue.28 , pp. 8045-8050
    • Bryliakov, K.P.1    Talsi, E.P.2
  • 37
    • 33646384377 scopus 로고    scopus 로고
    • Effect of added donor ligands on the selective oxygenation of organic sulfides by oxo(salen)chromium(V) complexes
    • DOI 10.1016/j.tet.2006.03.103, PII S0040402006005345
    • NS Venkataramanan S Rajagopal 2006 Tetrahedron 62 5645 10.1016/j.tet.2006.03.103 1:CAS:528:DC%2BD28Xkslyqsb0%3D (Pubitemid 43668795)
    • (2006) Tetrahedron , vol.62 , Issue.24 , pp. 5645-5651
    • Venkataramanan, N.S.1    Rajagopal, S.2
  • 38
    • 33846082691 scopus 로고    scopus 로고
    • Oxidation of methionines by oxochromium(V) cations: A kinetic and spectral study
    • DOI 10.1016/j.jinorgbio.2006.09.027, PII S0162013406002868
    • NS Venkataramanan S Rajagopal M Vairamani 2007 J Inorg Biochem 101 274 10.1016/j.jinorgbio.2006.09.027 1:CAS:528:DC%2BD2sXkvF2ntg%3D%3D (Pubitemid 46074157)
    • (2007) Journal of Inorganic Biochemistry , vol.101 , Issue.2 , pp. 274-282
    • Venkataramanan, N.S.1    Rajagopal, S.2    Vairamani, M.3
  • 39
    • 16344373749 scopus 로고    scopus 로고
    • Metal-salen complexes as efficient catalysts for the oxygenation of heteroatom containing organic compounds - Synthetic and mechanistic aspects
    • DOI 10.1016/j.ccr.2005.01.023
    • NS Venkataramanan G Kuppuraj S Rajagopal 2005 Coord Chem Rev 249 1249 10.1016/j.ccr.2005.01.023 1:CAS:528:DC%2BD2MXivVKntrg%3D (Pubitemid 40467516)
    • (2005) Coordination Chemistry Reviews , vol.249 , Issue.11-12 , pp. 1249-1268
    • Venkataramanan, N.S.1    Kuppuraj, G.2    Rajagopal, S.3
  • 40
    • 0031024261 scopus 로고    scopus 로고
    • Enantioselective catalytic ring opening of epoxides with carboxylic acids
    • DOI 10.1016/S0040-4039(96)02414-8, PII S0040403996024148
    • EN Jacobsen F Kakiuchi RG Konster JF Larrow M Tokunga 1997 Tetrahedron Lett 38 773 10.1016/S0040-4039(96)02414-8 1:CAS:528:DyaK2sXhtVKgtbw%3D (Pubitemid 27055855)
    • (1997) Tetrahedron Letters , vol.38 , Issue.5 , pp. 773-776
    • Jacobsen, E.N.1    Kakiuchi, F.2    Konsler, R.G.3    Larrow, J.F.4    Tokunaga, M.5
  • 41
    • 0001044547 scopus 로고    scopus 로고
    • 10.1021/jo980155d 1:CAS:528:DyaK1cXksVKrsbk%3D
    • MH Wu EN Jacobsen 1998 J Org Chem 63 5252 10.1021/jo980155d 1:CAS:528:DyaK1cXksVKrsbk%3D
    • (1998) J Org Chem , vol.63 , pp. 5252
    • Wu, M.H.1    Jacobsen, E.N.2
  • 42
    • 0033549570 scopus 로고    scopus 로고
    • 10.1002/(SICI)15 21-3773(199 90712)38:13/14<20 12::AID-AN IE2012>3.0. CO;2-H 1:C AS:528:Dy aK1MXkslSh trk%3D
    • MH Wu KB Hansen EN Jacobsen 1999 Angew Chem Int Ed 38 2012 10.1002/(SICI)1521-3773(19990712)38:13/14<2012::AID-ANIE2012>3.0.CO;2-H 1:CAS:528:DyaK1MXkslShtrk%3D
    • (1999) Angew Chem Int Ed , vol.38 , pp. 2012
    • Wu, M.H.1    Hansen, K.B.2    Jacobsen, E.N.3
  • 43
    • 0000971217 scopus 로고    scopus 로고
    • 10.1023/A:1019046411998 1:CAS:528:DC%2BD3cXmtVemtLc%3D
    • B Gigante A Corma H Garcia MJ Sabata 2000 Catal Lett 68 113 10.1023/A:1019046411998 1:CAS:528:DC%2BD3cXmtVemtLc%3D
    • (2000) Catal Lett , vol.68 , pp. 113
    • Gigante, B.1    Corma, A.2    Garcia, H.3    Sabata, M.J.4
  • 44
    • 0033225020 scopus 로고    scopus 로고
    • Polymer-supported salen complexes for heterogeneous asymmetric synthesis: Stability and selectivity
    • DOI 10.1002/(SI CI)1099-05 18(199911 01)37:21<38 88::AID-POLA 2>3.0.CO;2-B
    • MD Angelino PE Labinis 1999 J Polym Sci A Polym Chem 37 3888 10.1002/(SICI)1099-0518(19991101)37:21<3888::AID-POLA2>3.0.CO;2-B 1:CAS:528:DyaK1MXnt1Wgtb4%3D (Pubitemid 30538480)
    • (1999) Journal of Polymer Science, Part A: Polymer Chemistry , vol.37 , Issue.21 , pp. 3888-3898
    • Angelino, M.D.1    Laibinis, P.E.2
  • 45
    • 0033920416 scopus 로고    scopus 로고
    • 10.1021/ar960061v 1:CAS:528:DC%2BD3cXjtFKhsLY%3D
    • EN Jacobsen 2000 Acc Chem Res 33 421 10.1021/ar960061v 1:CAS:528:DC%2BD3cXjtFKhsLY%3D
    • (2000) Acc Chem Res , vol.33 , pp. 421
    • Jacobsen, E.N.1
  • 47
    • 0242432419 scopus 로고    scopus 로고
    • Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co salen-type complexes
    • DOI 10.1021/jo020191j
    • Y-M Shen W-L Duan M Shi 2003 J Org Chem 68 1559 10.1021/jo020191j 1:CAS:528:DC%2BD3sXhs1Krug%3D%3D (Pubitemid 36232523)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.4 , pp. 1559-1562
    • Shen, Y.-M.1    Duan, W.-L.2    Shi, M.3
  • 50
    • 0028067892 scopus 로고
    • Structure of protocatechuate 3,4-dioxygenase from Pseudomonas aeruginosa at 2.15 A resolution
    • DOI 10.1006/jmbi.1994.1754
    • DH Ohlendorf AM Orville JD Lipscomb 1994 J Mol Biol 244 586 10.1006/jmbi.1994.1754 1:CAS:528:DyaK2MXislegtLg%3D (Pubitemid 24381811)
    • (1994) Journal of Molecular Biology , vol.244 , Issue.5 , pp. 586-608
    • Ohlendorf, D.H.1    Orville, A.M.2    Lipscomb, J.D.3
  • 51
    • 0037040323 scopus 로고    scopus 로고
    • Iron(III)-salen complexes as enzyme models: Mechanistic study of oxo(salen)iron complexes oxygenation of organic sulfides
    • DOI 10.1021/jo010878o
    • VK Sivasubramanian M Ganesan S Rajagopal R Ramaraj 2002 J Org Chem 67 1506 10.1021/jo010878o 1:CAS:528:DC%2BD38XhtVKitb4%3D (Pubitemid 34211594)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.5 , pp. 1506-1514
    • Sivasubramanian, V.K.1    Ganesan, M.2    Rajagopal, S.3    Ramaraj, R.4
  • 52
    • 80053565712 scopus 로고    scopus 로고
    • Sivasubramanian VK, Ganesan M, Rajagopal S, Ramaraj R (unpublished work)
    • Sivasubramanian VK, Ganesan M, Rajagopal S, Ramaraj R (unpublished work)
  • 55
    • 4444245624 scopus 로고    scopus 로고
    • 10.1021/ic035360c 1:CAS:528:DC%2BD2cXhslyqtLs%3D
    • PJ Collman L Zeng I Brauman 2004 Inorg Chem 43 2672 10.1021/ic035360c 1:CAS:528:DC%2BD2cXhslyqtLs%3D
    • (2004) Inorg Chem , vol.43 , pp. 2672
    • Collman, P.J.1    Zeng, L.2    Brauman, I.3
  • 56
    • 0000254084 scopus 로고    scopus 로고
    • 10.1021/jo970463w
    • Z Groos S Ini 1997 J Org Chem 62 5514 10.1021/jo970463w
    • (1997) J Org Chem , vol.62 , pp. 5514
    • Groos, Z.1    Ini, S.2
  • 58
    • 0010463235 scopus 로고
    • 10.1016/0010-8545(93)85013-T 1:CAS:528:DyaK3sXltFKmsLc%3D
    • D Mansuy 1993 Coord Chem Rev 125 129 10.1016/0010-8545(93)85013-T 1:CAS:528:DyaK3sXltFKmsLc%3D
    • (1993) Coord Chem Rev , vol.125 , pp. 129
    • Mansuy, D.1
  • 62
    • 0027231963 scopus 로고
    • 10.1021/bi00064a014 1:CAS:528:DyaK3sXhs1CitL0%3D
    • DB Goodin DE Me Ree 1993 Biochemistry 32 3313 10.1021/bi00064a014 1:CAS:528:DyaK3sXhs1CitL0%3D
    • (1993) Biochemistry , vol.32 , pp. 3313
    • Goodin, D.B.1    Me Ree, D.E.2
  • 65
    • 31044453954 scopus 로고    scopus 로고
    • Catalytic epoxidation of olefins and hydroxylation of alkanes with sodium periodate by water-soluble manganese(III)salen
    • DOI 10.1016/j.molcata.2005.07.044, PII S1381116905005170
    • B Bahramian V Mirkhani S Tangestaninejad M Moghadam 2006 J Mol Cat A 244 139 10.1016/j.molcata.2005.07.044 1:CAS:528:DC%2BD28XovVWktg%3D%3D (Pubitemid 43121407)
    • (2006) Journal of Molecular Catalysis A: Chemical , vol.244 , Issue.1-2 , pp. 139-145
    • Bahramian, B.1    Mirkhani, V.2    Tangestaninejad, S.3    Moghadam, M.4
  • 69
    • 0039029808 scopus 로고
    • 10.1016/S0010-8545(00)82081-0 1:CAS:528:DyaE3sXhtFymurw%3D
    • MD Hobday TD Smith 1973 Coord Chem Rev 9 311 10.1016/S0010-8545(00)82081- 0 1:CAS:528:DyaE3sXhtFymurw%3D
    • (1973) Coord Chem Rev , vol.9 , pp. 311
    • Hobday, M.D.1    Smith, T.D.2
  • 70
    • 0037154923 scopus 로고    scopus 로고
    • Structure-reactivity correlation of anilines in acetic acid
    • DOI 10.1021/jo0158433
    • C Karunakaran M Kamalam 2002 J Org Chem 67 1118 10.1021/jo0158433 1:CAS:528:DC%2BD38XotVyrsg%3D%3D (Pubitemid 34182829)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.4 , pp. 1118-1124
    • Karunakaran, C.1    Kamalam, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.