Mechanism of hydroperoxide reduction by mangano-prostaglandin endoperoxide synthase

Biochemistry
L M Landino, L J Marnett

Abstract

Reaction of manganese-reconstituted prostaglandin endoperoxide synthase (Mn-PGHS) with 15-hydroperoxyeicosatetraenoic acid (15-HPETE) generates two products in nearly equal amounts: 15-hydroxyeicosatetraenoic acid (15-HETE) and 15-ketoeicosatetraenoic acid (15-KETE) [Kulmacz et al. (1994) Biochemistry 33, 5428-5439]. Their proposed mechanism to explain 15-KETE formation, namely oxidation of 15-HETE by the peroxidase activity of MnPGHS, was tested and found not to occur. Instead, 15-KETE may arise by one-electron reduction of 15-HPETE followed by oxidation of an intermediate alkoxyl radical. The mechanism of hydroperoxide reduction by Mn-PGHS was investigated using 10-hydroperoxyoctadeca-8,12-dienoic acid (10-OOH-18:2), a diagnostic probe of hydroperoxide reduction pathways. Reaction of Mn-PGHS with 10-OOH-18:2 generated the two-electron reduced product, 10-hydroxyoctadeca-8,12-dienoic acid (10-OH-18:2), as well as the one-electron reduction products, 10-oxooctadeca-8,12 dienoic acid (10-oxo-18:2) and 10-oxodec-8-enoic acid (10-oxo-10:1) in relative yields of 82, 10, and 7%, respectively. The identity of the one-electron reduction products was confirmed by electrospray ionization mass spectrometry. The detection of 10-oxo-10:1 p...Continue Reading

Citations

Aug 26, 1998·The American Journal of Medicine·D J Bjorkman
Sep 16, 1999·Biochemical Pharmacology·R LangenbachH Tiano
Apr 9, 2002·Prostaglandins & Other Lipid Mediators·Nannan ChenCarol Shoshkes Reiss
Jun 20, 2003·Progress in Lipid Research·Richard J KulmaczAh-Lim Tsai
Jan 23, 2003·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Pamela HardingSteven D Scherer
Sep 5, 2009·Archives of Biochemistry and Biophysics·Ah-Lim Tsai, Richard J Kulmacz
Dec 15, 2015·Journal of Trace Elements in Medicine and Biology : Organ of the Society for Minerals and Trace Elements (GMS)·Hans Jörg Leis, Werner Windischhofer
Apr 27, 2007·Archives of Biochemistry and Biophysics·Hui-Chun YehLee-Ho Wang
Mar 1, 2005·The Journal of Surgical Research·Steve A KellerToan Huynh
Mar 3, 2006·Journal of Inorganic Biochemistry·Thomas M MakrisStephen G Sligar
Jun 21, 2005·Free Radical Biology & Medicine·Duen-Suey ChouJoen-Rong Sheu
Apr 28, 2007·The Journal of Biological Chemistry·Jiayan LiuWilliam L Smith
Apr 16, 2015·International Surgery·Youichi KumagaiHideyuki Ishida
Jun 14, 2006·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Wen LiuRichard J Kulmacz
Jan 23, 2003·The Journal of Pharmacology and Experimental Therapeutics·David M AronoffJohn A Oates
Jul 3, 2020·European Journal of Organic Chemistry·Elisabeth Sitte, Mathias O Senge
Jun 12, 2003·Chemical Reviews·Carol A Rouzer, Lawrence J Marnett

❮ 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.