Toward Identification of the Compound I Reactive intermediate in Cytochrome P450 Chemistry: A QM/MM Study of Its EPA and Mössbauer Parameters.

Quantum mechanical/molecular mechanical (QM/MM) methods have been used in conjunction with density functional theory (DFT) and correlated ab initio methods to predict the electron paramagnetic resonance (EPR) and Mössbauer (MB) properties of Compound I in P450. For calibration purposes, a small Fe(I...

Full description

Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 127; no. 16; pp. 5840 - 5854
Main Authors: Schöneboom, Jan C., Neese, Frank, Thiel, Walter
Format: Article
Published: American Chemical Society 4/27/2005
Subjects:
Online Access:View this record in EBSCOhost
fields @attributes:
  recordID: 1
pdfLink:
plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=16924247&site=ehost-live
header:
  @attributes:
    shortDbName: hlh
    uiTerm: 16924247
    longDbName: Humanities International Complete
    uiTag: AN
  controlInfo:
    bkinfo:
    jinfo:
      jid:
        00027863
        ACS
      jtl: Journal of the American Chemical Society
      issn: 00027863
      maglogo: N
    pubinfo:
      dt: 4/27/2005
      vid: 127
      iid: 16
      pid: 997
      pub: American Chemical Society
    artinfo:
      ui:
        16924247
        10.1021/ja0424732
      ppf: 5840
      ppct: 14
      formats:
      tig:
        atl: Toward Identification of the Compound I Reactive intermediate in Cytochrome P450 Chemistry: A QM/MM Study of Its EPA and Mössbauer Parameters.
      aug:
        au:
          Schöneboom, Jan C.
          Neese, Frank
          Thiel, Walter
        affil:
          Max-Planck-Institut für Kohlenforschung, Kaiser- Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
          Max-Planck-Institut für Bioanorganische Chemie, Stiftstrasse 34-36, D-45413 Mülheim an der Ruhr, Germany
      su:
        Density functionals
        Electron paramagnetic resonance
        Functional analysis
        Magnetic resonance
        Atoms
        Chemistry
      sug:
        subj:
          Density functionals
          Electron paramagnetic resonance
          Functional analysis
          Magnetic resonance
          Atoms
          Chemistry
      ab: Quantum mechanical/molecular mechanical (QM/MM) methods have been used in conjunction with density functional theory (DFT) and correlated ab initio methods to predict the electron paramagnetic resonance (EPR) and Mössbauer (MB) properties of Compound I in P450. For calibration purposes, a small Fe(IV)-oxo complex [Fe(O)(NH)(HO)] was studied. The A and A states (in C, symmetry) are found to be within 0.1-0.2 eV. The large zero-field splitting (ZFS) of the (FeO) unit in the A state arises from spin-orbit coupling with the low-lying quintet and singlet states. The intrinsic g-anisotropy is very small. The spectroscopic properties of the model complex [Fe(O)(TMC)(CHCN)] (TMC = 1,4,8,- 11 -tetramethyl-1 ,4,8,11 -tetraazacyclotetradecane) are well reproduced by theory. In the model complexes [Fe(O)(TMP)(X)] (TMP = tetramesitylporphyrin, X = nothing or HO) the computations again account for the observed spectroscopic properties and predict that the coupling of the A state of the (FeO) unit to the porphyrin radical leads to a low-lying sextet/quartet manifold ∼12 kcal/mol above the quartet ground state. The calculations on cytochrome P450, with and without the simulation of the protein environment by point charges, predict a small antiferromagnetic coupling (J ≈ -13 to -16 cm; Ĥ = - 2JSS) and a large ZFS > 15 cm (with E/D ≈ 1/3) which will compete with the exchange coupling. This leads to three Kramers doublets of mixed multiplicity which are all populated at room temperature and may therefore contribute to the observed reactivity. The MB and ligand hyperline couplings (N, H) are fairly sensitive to the protein environment which controls the spin density distribution between the porphyrin ring and the axial cysteinate ligand.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
    refInfo:
    copyright:
      @attributes:
        flag: Y
      dt:
        @attributes:
          year: 2005
    holdings:
      @attributes:
        islocal: N