Spectral, electrochemical, and catalytic properties of a homologous series of manganese porphyrins as cytochrome P450 model: the effect of the degree of beta-bromination

Journal of Inorganic Biochemistry
Dayse C da SilvaYnara M Idemori

Abstract

A homologous series of beta-brominated porphyrins derived from meso-tetrakis(4-carbomethoxyphenyl)porphyrinatomanganese(III) chloride, i.e., Mn(III)(Br(x)TCMPP)Cl (x=0,2,4,6, and 8), was prepared and investigated as cytochrome P450 models. Hydroxylations of cyclohexane by iodosylbenzene (PhIO) and iodobenzene diacetate (PhI(OAc)(2)) in the presence or absence of water were carried out as P450 model reactions. The influence of the degree of beta-bromination of the macrocycle on the UV-vis spectra, the Mn(III)/Mn(II) reduction potential, and the catalytic properties of the Mn(III)(Br(x)TCMPP)Cl (x=0,2,4,6, and 8) series were examined. The catalytic efficiency does not correlate with the Mn(III)/Mn(II) reduction potential and shows a bell-shaped behavior, where the best results are achieved with the hexabrominated complex. Better hydroxylation yields were achieved by using PhI(OAc)(2) as oxygen donor, but at expenses of catalyst recovery; addition of water to this system resulted in a increase in the reaction rate. Recycling of the more oxidatively robust complexes Mn(III)(Br(6)TCMPP)Cl and Mn(III)(Br(8)TCMPP)Cl is feasible when using PhIO as oxygen donor. Selectivity and UV-vis data suggested that hydroxylation by both PhIO and P...Continue Reading

Citations

Jun 26, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shirley NakagakiKelly Aparecida Dias de Freitas Castro
Feb 27, 2017·Journal of Inorganic Biochemistry·Lucas B BolzonMarilda D Assis
Dec 2, 2017·Journal of Molecular Modeling·Higo de Lima Bezerra Cavalcanti, Gerd Bruno Rocha

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.