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medium-chain fatty acid omega-hydroxylase activity

Definition

Target type: molecularfunction

Catalysis of the reaction: an omega-methyl-medium-chain fatty acid + O2 + reduced [NADPH--hemoprotein reductase] = an omega-hydroxy-medium-chain fatty acid + H+ + H2O + oxidized [NADPH--hemoprotein reductase]. A medium-chain fatty acid has an aliphatic tail containing 6 to 12 carbons. [PMID:35934685, RHEA:75279]

Medium-chain fatty acid omega-hydroxylase activity is a crucial enzymatic process responsible for the hydroxylation of medium-chain fatty acids at the terminal carbon atom. This reaction involves the addition of a hydroxyl group (-OH) to the omega (ω) position of the fatty acid chain, leading to the formation of a ω-hydroxy fatty acid. The enzyme catalyzing this reaction is known as medium-chain fatty acid omega-hydroxylase (MCOH), and it plays a vital role in various metabolic pathways, including the biosynthesis of specific lipids and the detoxification of harmful fatty acids.

The primary function of MCOH is to introduce a hydroxyl group at the ω-carbon atom, thereby converting a saturated fatty acid into a ω-hydroxy fatty acid. This hydroxylation reaction requires molecular oxygen (O2) and a reducing cofactor, such as NADPH, as substrates. The mechanism involves the activation of molecular oxygen by the enzyme, which then oxidizes the fatty acid substrate.

The ω-hydroxy fatty acids produced by MCOH serve as precursors for various downstream metabolic processes. In particular, they play a crucial role in the biosynthesis of specific lipids, such as prostaglandins, leukotrienes, and lipoxins, which are involved in inflammation, immune responses, and other physiological functions.

Moreover, MCOH contributes to the detoxification of harmful fatty acids. By hydroxylating these fatty acids, the enzyme converts them into less toxic metabolites that can be more easily eliminated from the body. This detoxification mechanism is particularly important for preventing the accumulation of harmful fatty acids in tissues, which can lead to various pathological conditions.

Overall, medium-chain fatty acid omega-hydroxylase activity is an essential enzymatic process that plays a critical role in lipid metabolism, inflammation, and detoxification. Its function is to introduce a hydroxyl group at the ω-carbon atom of medium-chain fatty acids, leading to the formation of ω-hydroxy fatty acids, which serve as precursors for various important metabolic pathways.'
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Proteins (1)

ProteinDefinitionTaxonomy
Cytochrome P450 4A22A cytochrome P450 4A22 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q5TCH4]Homo sapiens (human)

Compounds (4)

CompoundDefinitionClassesRoles
tranylcypromine(1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.

tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).

Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)
2-phenylcyclopropan-1-amine
proadifen hydrochloride
pirlindolepirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812carbazoles
kaf156ganaplacide: antimalarial