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Concept

Hydroxylation

In chemistry, hydroxylation can refer to: (i) most commonly, hydroxylation describes a chemical process that introduces a hydroxyl group () into an organic compound. (ii) the degree of hydroxylation refers to the number of OH groups in a molecule. The pattern of hydroxylation refers to the location of hydroxy groups on a molecule or material. Installing hydroxyl groups into organic compounds can be effected by various metal catalysts. Many such catalysts are biomimetic, i.e. they are inspired by or intended to mimic enzymes such as cytochrome P450. Whereas many hydroxylations insert O atoms into bonds, some reactions add OH groups to unsaturated substrates. The Sharpless dihydroxylation is such a reaction: it converts alkenes into diols. The hydroxy groups are provided by hydrogen peroxide, which adds across the double bond of alkenes. In biochemistry, hydroxylation reactions are often facilitated by enzymes called hydroxylases. A bond is converted to an alcohol by insertion of an oxygen atom into a bond. Typical stoichiometries for the hydroxylation of a generic hydrocarbon are these: 2R3C-H + O2 -> 2R3C-OH R3C-H + O2 + 2e- + 2H+ -> R3C-OH + H2O Since itself is a slow and unselective hydroxylating agent, catalysts are required to accelerate the pace of the process and to introduce selectivity. Hydroxylation is often the first step in the degradation of organic compounds in air. Hydroxylation is important in detoxification since it converts lipophilic compounds into water-soluble (hydrophilic) products that are more readily removed by the kidneys or liver and excreted. Some drugs (for example, steroids) are activated or deactivated by hydroxylation. The principal hydroxylation agent in nature is cytochrome P-450, hundreds of variations of which are known. Other hydroxylating agents include flavins, alpha-ketoglutarate-dependent hydroxylases, and some diiron hydroxylases. The hydroxylation of proteins occurs as a post-translational modification, and is catalyzed by 2-oxoglutarate-dependent dioxygenases.

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