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Hydroxylation

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Hydroxylation is any chemical process that introduces one or more hydroxyl groups (-OH) into a compound (or radical) thereby oxidising it. In biochemistry, hydroxylation reactions are often facilitated by enzymes called hydroxylases.

[edit] Hydroxylation in proteins

Proline is the principal residue to be hydroxylated in proteins, which occurs at the <math>\mathrm{C^{\gamma}}</math> atom, forming hydroxyproline (Hyp), an essential element of collagen, in turn a necessary element of connective tissue. In some cases, proline may be hydroxylated instead on its <math>\mathrm{C^{\beta}}</math> atom. Lysine may also be hydroxylated on its <math>\mathrm{C^{\delta}}</math> atom, forming hydroxylysine (Hyl).

These three reactions are catalyzed by very large, multi-subunit enzymes prolyl 4-hydroxylase, prolyl 3-hydroxylase and lysyl 5-hydroxylase, respectively. These reactions require iron (as well as molecular oxygen and α-ketoglutarate) to carry out the oxidation, and use ascorbic acid (vitamin C) to return the iron to its reduced state. Deprivation of ascorbate leads to deficiencies in proline hydroxylation, which leads to less stable collagen, which can manifest itself as the disease scurvy. Since vitamin C is rich in citrus fruits, British sailors were given limes to combat scurvy on long ocean voyages; hence, they were called "lymies".

[edit] See also


Protein primary structure and posttranslational modifications
General: Protein biosynthesis | Peptide bond | Proteolysis | Racemization | N-O acyl shift
N-terminus: Acetylation | Formylation | Myristoylation | Pyroglutamate | methylation | glycation | myristoylation (Gly) | carbamylation
C-terminus: Amidation | Glycosyl phosphatidylinositol (GPI) | O-methylation | glypiation | ubiquitination | sumoylation
Lysine: Methylation | Acetylation | Acylation | Hydroxylation | Ubiquitination | SUMOylation | Desmosine | deamination and oxidation to aldehyde| O-glycosylation | imine formation | glycation | carbamylation
Cysteine: Disulfide bond | Prenylation | Palmitoylation
Serine/Threonine: Phosphorylation | Glycosylation
Tyrosine: Phosphorylation | Sulfation | porphyrin ring linkage | flavin linkage | GFP prosthetic group (Thr-Tyr-Gly sequence) formation | Lysine tyrosine quinone (LTQ) formation | Topaquinone (TPQ) formation
Asparagine: Deamidation | Glycosylation
Aspartate: Succinimide formation
Glutamine: Transglutamination
Glutamate: Carboxylation | polyglutamylation | polyglycylation
Arginine: Citrullination | Methylation
Proline: Hydroxylation
←Amino acids Secondary structure→
fr:Hydroxylation

it:Idrossilazione sv:Hydroxylering

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