Publikation: NIH shift in flavin-dependent monooxygenation : mechanistic studies with 2-aminobenzoyl-CoA monooxygenase/reductase
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The flavoprotein 2-aminobenzoyl-CoA monooxygenase/reductase from the eubacterium Azoarcus evansii catalyzes the dearomatization of 2-aminobenzoyl-CoA. The reaction consists in an O2-dependent monooxygenation at the benzene position 5, which is followed immediately by an NADH-dependent hydrogenation of the intermediate at the same catalytic locus. The reaction was studied by 1H, 2H, and 13C NMR spectroscopy of the products. The main product was characterized as 5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA by two-dimensional NMR spectroscopy. Thus, [5-2H]2-aminobenzoyl-CoA was converted into [6-2H]5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA, indicating a 5 → 6 shift of the [5-2H] label. Label from NAD2H was transferred to the 3 position of the cyclic eneamine, whereas label from solvent D2O was incorporated into the 4 and the 6 positions of 5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA. The labeling pattern is compatible with the monooxygenation proceeding via what is formally an NIH shift, yielding 5-oxo-2-aminocyclohex-1,3-diene-1-carboxyl-CoA as a protein-bound intermediate. It is suggested that this shift in flavin-dependent monooxygenation may have general validity.
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HARTMANN, Steffen, Claus HULTSCHIG, Wolfgang EISENREICH, Georg FUCHS, Adelbert BACHER, Sandro GHISLA, 1999. NIH shift in flavin-dependent monooxygenation : mechanistic studies with 2-aminobenzoyl-CoA monooxygenase/reductase. In: PNAS [ Proceedings of the National Academy of Sciences ]. 1999, 96(14), pp. 7831-7836BibTex
@article{Hartmann1999shift-7944, year={1999}, title={NIH shift in flavin-dependent monooxygenation : mechanistic studies with 2-aminobenzoyl-CoA monooxygenase/reductase}, number={14}, volume={96}, journal={PNAS [ Proceedings of the National Academy of Sciences ]}, pages={7831--7836}, author={Hartmann, Steffen and Hultschig, Claus and Eisenreich, Wolfgang and Fuchs, Georg and Bacher, Adelbert and Ghisla, Sandro} }
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