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Encyclopedia > Tyrosine
Tyrosine
Chemical structure of Tyrosine Chemical structure of Tyrosine
Systematic name (S)-2-Amino-3-(4-hydroxy-
phenyl)-propanoic acid
Abbreviations Tyr
Y
Chemical formula C9H11NO3
Molecular mass 181.19 g mol-1
Melting point 343 °C
Density 1.456 g cm-3
Isoelectric point 5.66
pKa 2.24
9.04
10.10
Molar extinction coefficient 1420 M-1 cm-1 at 274.6 nm
PubChem 1153
CAS number [60-18-4]
EINECS number 200-460-4
SMILES N[C@@H](Cc1ccc(O)cc1)C(O)=O
Absorption and emission spectrum
Absorption (blue) and fluorescence (red) of tyrosine in water (pH 7)

Absorbance and fluorescence of tyrosine in water/buffer Image File history File links Download high resolution version (2000x1643, 30 KB) Licensing File links The following pages link to this file: Amino acid Tyrosine User:Benjah-bmm27/Gallery ... Image File history File links Download high-resolution version (706x718, 27 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Tyrosine User:Benjah-bmm27/Old gallery Tyrosine (data page) ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... The isoelectric point (pI) is the pH at which a molecule or surface carries no net electrical charge. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... In analytical chemistry, the molar absorptivity or molar extinction coefficient ε of a chemical species at a given wavelength is a measure of how strongly the species absorbs light at that wavelength. ... PubChem is a database of chemical molecules. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A materials absorption spectrum shows the fraction of incident electromagnetic radiation absorbed by the material over a range of frequencies. ... A materials emission spectrum is the amount of electromagnetic radiation of each frequency it emits when it is heated (or more generally when it is excited). ... Image File history File links Download high-resolution version (2208x1444, 132 KB) Sample: Tyrosine dissolved in water, 0. ...

Disclaimer and references

Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese[1][2]), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins. It has a phenol side chain with a hydroxyl group. Upon the location of the hydroxyl group, there are three structural isomers of Tyr, namely para-Tyr (p-Tyr), meta-Tyr (m-Tyr) and ortho-Tyr (o-Tyr). Enzymatically, only the first isomer (p-Tyr) is produced from L-Phe by the Phe-hydroxylase enzyme. The other two isoforms, m-Tyr and o-Tyr can be produced as a consequence of free radical attack on Phe in states with increased oxidative stress. Freiherr Justus von Liebig (May 12, 1803 in Darmstadt, Germany – April 18, 1873 in Munich, Germany) was a German chemist who made major contributions to agricultural and biological chemistry, and worked on the organization of organic chemistry. ... Phenylalanine is one of the standard amino acids. ... Drawing of the structure of cork as it appeared under the microscope to Robert Hooke from Micrographia which is the origin of the word cell being used to describe the smallest unit of a living organism Cells in culture, stained for keratin (red) and DNA (green) The cell is the... An overview of protein synthesis. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ... Oxidative stress is a medical term for damage to animal or plant cells (and thereby the organs and tissues composed of those cells) caused by reactive oxygen species, which include (but are not limited to) superoxide, singlet oxygen, peroxynitrite or hydrogen peroxide. ...

Tyrosine is converted to levodopa by the enzyme tyrosine hydroxylase. Image File history File links Phe_Tyr. ... L-DOPA (levodopa, 3,4-dihydroxy-L-phenylalanine). ... Tyrosine Hydroxylase is the enzyme responsible for catalysing the conversion of L-tyrosine, an amino acid, to dihydroxyphenylalanine (DOPA), a precursor to Dopamine in the process the body uses to synthesise adrenaline (epinephrin). ...


Some of the tyrosine residues can be tagged with a phosphate group (phosphorylated) by protein kinases. (In its phosphorylated state, it is referred to as phosphotyrosine.). Tyrosine phosphorylation is considered as one of the key steps in signal transduction and regulation of enzymatic activity. Phosphotyrosine can be detected through specific antibodies. Tyrosine residues may also be modified by the addition of a sulfate group, a process known as tyrosine sulfation. Tyrosine sulfation is catalyzed by tyrosylprotein sulfotransferase (TPST). Like the phosphotyrosine antibodies mentioned above, antibodies have recently been described that specifically detect sulfotyrosine. Tyrosine is also precursor to the thyroid hormones thyroxine and triiodothyronine, the pigment melanin, and the biologically-active catecholamines dopamine, norepinephrine and epinephrine. A phosphorylated serine residue Phosphorylation is the addition of a phosphate (PO4) group to a protein or a small molecule or the introduction of a phosphate group into an organic molecule. ... A protein kinase is an enzyme that modifies other proteins by chemically adding phosphate groups to them (phosphorylation). ... Tyrosine sulfation is a posttranslational modification where a sulfate group is added to a tyrosine residue of a protein molecule. ... Tyrosine sulfation is a posttranslational modification where a sulfate group is added to a tyrosine residue of a protein molecule. ... Norepinephrine A hormone (from Greek όρμή - to set in motion) is a chemical messenger from one cell (or group of cells) to another. ... Thyroxine, or 3:5,3:5 tetra­iodothyronine (often abbreviated as T4) is the major hormone secreted by the follicular cells of the thyroid gland. ... The thyroid hormones, thyroxine (T4) and triiodothyronine (T3), are tyrosine-based hormones produced by the thyroid gland. ... Broadly, melanin is any of the polyacetylene, polyaniline, and polypyrrole blacks and browns or their mixed copolymers. ... tyrosine is the precursor of catecholamines epinephrine norepinephrine dopamine Synthesis Catecholamines are chemical compounds derived from the amino acid tyrosine containing catechol and amine groups. ... Dopamine is a phenethylamine naturally produced by the human body. ... Norepinephrine (INN)(abbr. ... “Adrenaline” redirects here. ...


In Papaver somniferum, the opium poppy, it is used to produce morphine. The Opium Poppy, Papaver somniferum, is the type of poppy from which opium and all refined opiates such as heroin are extracted, as well as an important food item. ... Morphine (INN) (IPA: ) is a highly potent opiate analgesic drug and is the principal active agent in opium and the prototypical opiate. ...


Biosynthesis

Tyrosine cannot be completely synthesized by animals, although it can be made by hydroxylation of phenylalanine if the latter is in abundant supply. It is produced by plants and most microorganisms from prephenate, an intermediate on the shikimate pathway. Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ... Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine. ... Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. ...


Prephenate is oxidatively decarboxylated with retention of the hydroxyl group to give p-hydroxyphenylpyruvate. This is transaminated using glutamate as the nitrogen source to give tyrosine and α-ketoglutarate. The most fundamental reactions in chemistry are the redox processes. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Transamination is the reaction between an amino acid and an alpha-keto acid. ... Glutamic acid (Glu, E), is the protonated form of glutamate (the anion). ... Ketoglutaric acid is used for either of two crystalline keto derivatives C5H6O5 of glutaric acid. ...


Image File history File links Download high resolution version (1557x442, 15 KB) Description: Biosynthesis of tyrosine. ...


Tyrosine hydroxylase

Tyrosine hydroxylase (TH) is the rate-limiting enzyme involved in the synthesis of the catecholamines such as dopamine, norepinephrine and epinephrine. Tyrosine Hydroxylase is the enzyme responsible for catalysing the conversion of L-tyrosine, an amino acid, to dihydroxyphenylalanine (DOPA), a precursor to Dopamine in the process the body uses to synthesise adrenaline (epinephrin). ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Catecholamines are chemical compounds derived from the amino acid tyrosine that act as hormones or neurotransmitters. ... Dopamine is a phenethylamine naturally produced by the human body. ... Norepinephrine (INN)(abbr. ... “Adrenaline” redirects here. ...


Medical use

L-Tyrosine is sometimes recommended by practitioners as helpful for weight loss, clinical depression, Parkinson's Disease, Attention Deficit Disorder and phenylketonuria; however, one study found that it had no impact on endurance exercise performance. [3] This article needs additional references or sources for verification. ... Clinical depression (also called major depressive disorder, or unipolar depression when compared to bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... PhenylKetonUria (PKU) is an autosomal recessive genetic disorder characterized by a deficiency in the enzyme phenylalanine hydroxylase (PAH). ...


See also

Tyramine (4-hydroxy-phenethylamine) is a monoamine compound derived from the amino acid tyrosine. ... Alkaptonuria also known as alcaptonuria or ochronosis is a rare inherited genetic disorder of tyrosine metabolism. ... Tyrosinemia (or Tyrosinaemia) is an error of metabolism, usually inborn, in which the body can not effectively break down the amino acid tyrosine, found in most animal and plant proteins. ... Albinism (from Latin albus; extended etymology), more technically hypomelanism or hypomelanosis, is a form of hypopigmentary congenital disorder, characterized by a lack of melanin pigment in the eyes, skin and hair (or more rarely the eyes alone). ... Tyrosine sulfation is a posttranslational modification where a sulfate group is added to a tyrosine residue of a protein molecule. ...

References

  • AJ Hoffhines et al. Journal of Biological Chemistry 281:37877-37887, 2006[1]
  • GA Molnar et al. Kidney International 68:2281-2287, 2005 Abstract
  • GA Molnar et al. Free Radical Research 39(12):1359-1366, 2005 Abstract

Notes

  1. ^ Tyrosine at infoplease.com
  2. ^ Tyrosine at etymonline.com
  3. ^ Parcell A.C., et al. Effects of L-tyrosine and carbohydrate ingestion on performance. Journal of Applied Physiology 2002 Nov; 93(5): 1590-97. Abstract

External links

  • Phenylalanine and tyrosine biosynthesis
  • Computational Chemistry Wiki
  • Phosphotyrosine Antibody review



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Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: The 20 Common Amino Acids Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)

  Results from FactBites:
 
Tyrosine - Wikipedia, the free encyclopedia (247 words)
Tyrosine (from the Greek tyros, meaning "cheese", as it was first discovered in cheese), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins.
Tyrosine is converted to DOPA by Tyrosine hydroxylase, an enzyme.
Tyrosine hydroxylase (TH) is the rate-limiting enzyme involved in the synthesis of the catecholamines.
Tyrosine kinase - Wikipedia, the free encyclopedia (458 words)
A tyrosine kinase (EC 2.7.1.112) is an enzyme that can transfer a phosphate group to a tyrosine residue in a protein; these enzymes are a subgroup of the larger class of protein kinases.
The hormones that act on tyrosine kinase receptors are generally growth hormones and factors that promote cell division (e.g., insulin, insulin-like growth factor 1, epidermal-derived growth factor).
An example is PDB 1IRK, the crystal structure of the tyrosine kinase domain of the human insulin receptor.
  More results at FactBites »

 
 

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