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Hydroxyproline

 

 
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Hydroxyproline
 
 
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4-Hydroxyproline, or hydroxyproline (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
5H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
9O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
), is an uncommon amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
, abbreviated as HYP, e.g., in Protein Data Bank
Protein Data Bank

The Protein Data Bank is a repository for the 3-D structural data of large biological molecules, such as proteins and nucleic acids. . The data, typically obtained by X-ray crystallography or Protein NMR and submitted by biologists and biochemistry from around the world, are released into the public domain, and can be accessed at no charge...
.

oxyproline differs from proline
Proline

Proline is an a-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that humans can synthesize it....
 by the presence of a hydroxyl (OH) group attached to the C (gamma) atom.

Other hydroxyprolines also exist in nature, notably 2,3-cis-3,4-trans-3,4-dihydroxyproline which occurs in diatom
Diatom

Diatoms are a major group of eukaryote algae, and are one of the most common types of phytoplankton. Most diatoms are unicellular, although they can exist as Colony in the shape of filaments or ribbons , fans , zigzags , or stellate colonies ....
 cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
s and is postulated to have a role in silica deposition.






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4-Hydroxyproline, or hydroxyproline (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
5H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
9O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
), is an uncommon amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
, abbreviated as HYP, e.g., in Protein Data Bank
Protein Data Bank

The Protein Data Bank is a repository for the 3-D structural data of large biological molecules, such as proteins and nucleic acids. . The data, typically obtained by X-ray crystallography or Protein NMR and submitted by biologists and biochemistry from around the world, are released into the public domain, and can be accessed at no charge...
.

Structure

Hydroxyproline differs from proline
Proline

Proline is an a-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that humans can synthesize it....
 by the presence of a hydroxyl (OH) group attached to the C (gamma) atom.

Other hydroxyprolines also exist in nature, notably 2,3-cis-3,4-trans-3,4-dihydroxyproline which occurs in diatom
Diatom

Diatoms are a major group of eukaryote algae, and are one of the most common types of phytoplankton. Most diatoms are unicellular, although they can exist as Colony in the shape of filaments or ribbons , fans , zigzags , or stellate colonies ....
 cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
s and is postulated to have a role in silica deposition. Hydroxyproline is also found in the walls of oomycetes, fungus-like protists related to diatoms.

Production and function

Hydroxyproline is produced by hydroxylation
Hydroxylation

Hydroxylation is any chemistry process that introduces one or more hydroxyl groups into a compound thereby oxidation it. In biochemistry, hydroxylation reactions are often facilitated by enzymes called hydroxylases....
 of the amino acid proline
Proline

Proline is an a-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that humans can synthesize it....
 by the enzyme prolyl hydroxylase
Prolyl hydroxylase

Prolyl hydroxylase is an enzyme involved in the production of collagen, acting to hydroxylate proline to hydroxyproline.It requires vitamin C as a cofactor....
 following protein synthesis (as a post-translational modification). The enzyme catalysed reaction takes place in the lumen of the endoplasmic reticulum.

Hydroxyproline is a major component of the protein
Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
 collagen
Collagen

Collagen is the main protein of connective tissue in animals and the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content....
. Hydroxyproline and proline play key roles for collagen stability. They permit the sharp twisting of the collagen helix. In the canonical collagen Xaa-Yaa-Gly triad (where Xaa and Yaa are any amino acid), a proline occupying the Yaa position is hydroxylated to give a Xaa-Hyp-Gly sequence. This modification of the proline residue increases the stability of the collagen triple helix. It was initially proposed that the stabilization was due to water molecules forming a hydrogen bonding network linking the prolyl hydroxyl groups and the main-chain carbonyl groups. It was subsequently shown that the increase in stability is primarily through stereoelectronic effects and that hydration of the hydroxyproline residues provides little or no additional stability.

Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin
Elastin

Elastin is a protein in connective tissue that is Elasticity and allows many tissues in the body to resume their shape after stretching or contracting....
. For this reason, hydroxyproline content has been used as an indicator to determine collagen
Collagen

Collagen is the main protein of connective tissue in animals and the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content....
 and/or gelatin
Gelatin

Gelatin is a translucent, colorless, brittle, nearly tasteless solid, derived from the collagen inside animals' skin and mostly bones. It has been commonly used as a gelling agent in food, pharmaceutical, photography, and cosmetic manufacturing....
 amount.

Clinical significance

Proline
Proline

Proline is an a-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that humans can synthesize it....
 hydroxylation requires ascorbic acid
Ascorbic acid

Ascorbic acid is a sugar acid with antioxidant properties. Its appearance is white to light-yellow crystals or powder. It is water-soluble. The L-enantiomer of ascorbic acid is commonly known as vitamin C....
. The most obvious, first effects (gum and hair problems) of absence of ascorbic acid
Ascorbic acid

Ascorbic acid is a sugar acid with antioxidant properties. Its appearance is white to light-yellow crystals or powder. It is water-soluble. The L-enantiomer of ascorbic acid is commonly known as vitamin C....
 in humans come from the resulting defect in hydroxylation
Hydroxylation

Hydroxylation is any chemistry process that introduces one or more hydroxyl groups into a compound thereby oxidation it. In biochemistry, hydroxylation reactions are often facilitated by enzymes called hydroxylases....
 of proline
Proline

Proline is an a-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that humans can synthesize it....
 residues of collagen
Collagen

Collagen is the main protein of connective tissue in animals and the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content....
, with reduced stability
Chemical stability

Chemical stability when used in the technical sense in chemistry, means thermodynamic stability of a chemical system.Thermodynamic stability occurs when a system is in its lowest energy state, or chemical equilibrium with its environment....
 of the collagen molecule causing scurvy
Scurvy

Scurvy is a disease resulting from a deficiency of vitamin C, which is required for the synthesis of collagen in humans. The chemical name for vitamin C, ascorbic acid, is derived from the Latin name of scurvy, scorbutus....
.

See also

  • Imino acid
    Imino acid

    In chemistry, an imino acid is any molecule that contains both imine and carboxyl functional groups.Imino acids are related to amino acids, which contain both amino and carboxyl functional groups....
  • Hydroxylysine
    Hydroxylysine

    5-Hydroxylysine is an amino acid with the molecular formula C6H14N2O3. It is a hydroxy derivative of lysine....


External links

  • [https://simtk.org/home/hydroxyproline Molecular mechanics parameters]


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