Aliphatic C-H Bond Halogenation by Iron(II)-α-Keto Acid Complexes and O2 : Functional Mimicking of Nonheme Iron Halogenases

Inorganic Chemistry
Rahul Dev JanaTapan Kanti Paine

Abstract

α-Ketoglutarate-dependent nonheme halogenases catalyze the halogenation of aliphatic C-H bonds in the biosynthesis pathway of many natural products. An iron(IV)-oxo-halo species has been established as the active oxidant in the halogenation reactions. With an objective to emulate the function of the nonheme halogenases, two iron(II)-α-keto acid complexes, [(phdpa)Fe(BF)Cl] (1) and [(1,4-tpbd)Fe2(BF)2Cl2] (2) (where phdpa = N,N-bis(2-pyridylmethyl)aniline, 1,4-tpbd = N,N, N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine, and BF = benzoylformate), have been prepared. The iron complexes are capable of carrying out the oxidative halogenation of aliphatic C-H bonds using O2 as the terminal oxidant. Although the complexes are not selective toward C-H bond halogenation, they are the only examples of nonheme iron(II)-α-keto acid complexes mimicking the activity of nonheme halogenases. The dinuclear complex (2) exhibits enhanced reactivity toward C-H bond halogenation/hydroxylation.

References

Aug 2, 2006·Inorganic Chemistry·Jan-Uwe RohdeLawrence Que
Jan 16, 2007·Nature Chemical Biology·Danica P GalonićCarsten Krebs
Jun 5, 2007·Accounts of Chemical Research·Carsten KrebsJ Martin Bollinger
Oct 18, 2007·Journal of the American Chemical Society·Danica Galonić FujimoriPamela J Riggs-Gelasco
Mar 14, 2009·Journal of the American Chemical Society·Cintyu WongCatherine L Drennan
Oct 10, 2009·Proceedings of the National Academy of Sciences of the United States of America·Megan L MatthewsJ Martin Bollinger
May 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Shanthi PandianNeil A Burton
May 12, 2010·Chemistry : a European Journal·Peter Comba, Steffen Wunderlich
Jul 28, 2010·Proceedings of the National Academy of Sciences of the United States of America·Dheeraj KhareJanet L Smith
Jul 12, 2011·Journal of the American Chemical Society·Jason EnglandLawrence Que
Mar 2, 2013·The Journal of Biological Chemistry·Heather J Kulik, Catherine L Drennan
Oct 19, 2013·Chemical Communications : Chem Comm·Anil Kumar VardhamanSam P de Visser
Aug 6, 2014·Chemical Communications : Chem Comm·Oriol PlanasMiquel Costas
May 13, 2015·Journal of the American Chemical Society·Ryan J MartinieAlexey Silakov
Feb 16, 2016·Journal of the American Chemical Society·Mayank PuriLawrence Que

❮ Previous
Next ❯

Citations

Sep 6, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Ramamoorthy RamasubramanianRamasamy Mayilmurugan

❮ 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.