Manganese substituted Compound I of cytochrome P450 biomimetics: A comparative reactivity study of MnV-oxo versus MnIV-oxo species

Latifi, Reza; Tahsini, Laleh; Karamzadeh, Baharan; Safari, Nasser; Nam, Wonwoo; Visser, Sam P. de

doi:10.1016/j.abb.2010.12.035

Cited by 40 publications

(18 citation statements)

References 82 publications

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“…DFT calculations provided some insight into the different reaction pathways observed for Mn V (O) vs. Mn IV (O) with AcrH 2 . 144 In the case of Mn IV (O), an H-atom abstraction is more thermodynamically favored than overall hydride transfer, whereas with Mn V (O), hydride abstraction is more favored. The Mn V (O) was described as the more potent oxidant with that substrate.…”

Section: Metal-oxo Porphyrinoid Complexes As Models For Biological Oxmentioning

confidence: 99%

Biomimetic Reactivity of Oxygen-Derived Manganese and Iron Porphyrinoid Complexes

2017

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Heme proteins utilize the heme cofactor, an iron porphyrin, to perform a diverse range of reactions including dioxygen binding and transport, electron transfer, and oxidation/oxygenations. These reactions share several, key metalloporphyrin intermediates, typically derived from dioxygen and its congeners such as hydrogen peroxide, and which are comprised of metal-dioxygen, metal-superoxo, metal-peroxo, and metal-oxo adducts. A wide variety of synthetic metalloporphyrinoid complexes have been synthesized to generate and stabilize these intermediates, and then employed to determine the spectroscopic features, structures, and reactivities of such species in controlled and well-defined environments. In this review, we summarize recent findings on the reactivity of these species with common porphyrinoid scaffolds employed for biomimetic studies. The proposed mechanisms of action are emphasized. The review is organized by structural type of metal-oxygen intermediate, and broken into subsections based on the metal (manganese, iron) and porphyrinoid ligand (porphyrin, corrole, corrolazine).

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Section: Metal-oxo Porphyrinoid Complexes As Models For Biological Oxmentioning

confidence: 99%

Biomimetic Reactivity of Oxygen-Derived Manganese and Iron Porphyrinoid Complexes

2017

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“…For example, the reactivity of the Mn V ‐oxo porphyrin complex is 150 times greater than that of the Mn IV ‐oxo porphyrin complex in the oxidation of xanthene. [22d] Furthermore, computational studies show that the Mn V ‐oxo porphyrin complex and Mn IV ‐oxo porphyrin complex are capable of hydroxylating 10‐methyl‐9,10‐dihydroacridine, and the Mn V ‐oxo porphyrin complex is the more active oxidant, based on the result of density functional theory (DFT) calculations . Besides, Mn V ‐oxo porphyrin complexes are commonly regarded as active species in oxygen‐atom transfer reactions and chlorite oxidation reactions .…”

Section: Resultsmentioning

confidence: 99%

Mechanistic Understanding towards the Role of Cyclohexene in Enhancing the Efficiency of Manganese Porphyrin‐Catalyzed Aerobic Oxidation of Diphenylmethane

et al. 2018

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The selective aerobic oxidation of nonactivated C-H bonds is a key challenge in both industrial and academic research. The catalytic activity of manganese porphyrins (MnTPPCl) towards the aerobic oxidation of diphenylmethane (DPM) is investigated. Compared with the oxidation-catalyzed MnTPPCl alone, the conversion of DPM is enhanced ca. 6 times (from 7.0 % to 42.5 %) in the presence of cyclohexene. Some in situ characterizations, such as in situ EPR (electron paramag-[a] Fine

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“…In the particular case of manganese porphyrins (MnP), the substituents make the catalyst more reactive: they destabilize the active species Mn V (O), which facilitates oxygen atom transfer from this species to the substrate and increases product yield [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Biomimetic alkane oxidation by iodosylbenzene and iodobenzene diacetate catalyzed by a new manganese porphyrin: Water effect

Silva

Idemori

DeFreitas-Silva

2015

Applied Catalysis A: General

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Manganese substituted Compound I of cytochrome P450 biomimetics: A comparative reactivity study of MnV-oxo versus MnIV-oxo species

Cited by 40 publications

References 82 publications

Biomimetic Reactivity of Oxygen-Derived Manganese and Iron Porphyrinoid Complexes

Biomimetic Reactivity of Oxygen-Derived Manganese and Iron Porphyrinoid Complexes

Mechanistic Understanding towards the Role of Cyclohexene in Enhancing the Efficiency of Manganese Porphyrin‐Catalyzed Aerobic Oxidation of Diphenylmethane

Biomimetic alkane oxidation by iodosylbenzene and iodobenzene diacetate catalyzed by a new manganese porphyrin: Water effect

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