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Tyrosine information


Tyrosine
Skeletal formula of the L-isomer
Skeletal formula of L-tyrosine

L-Tyrosine at physiological pH
ball-and-stick model[1]
space-filling model[1]
Names
IUPAC name
(S)-Tyrosine
Other names
L-2-Amino-3-(4-hydroxyphenyl)propanoic acid
Identifiers
CAS Number
  • 60-18-4 (L) checkY
3D model (JSmol)
  • Interactive image
  • Zwitterion: Interactive image
ChEBI
  • CHEBI:17895 checkY
ChEMBL
  • ChEMBL925 checkY
ChemSpider
  • 5833 checkY
DrugBank
  • DB00135 checkY
ECHA InfoCard 100.000.419 Edit this at Wikidata
IUPHAR/BPS
  • 4791
KEGG
  • C00082
PubChem CID
  • 6057
UNII
  • 42HK56048U checkY
CompTox Dashboard (EPA)
  • DTXSID1023730 Edit this at Wikidata
InChI
  • InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 checkY
    Key: OUYCCCASQSFEME-QMMMGPOBSA-N checkY
  • Key: OUYCCCASQSFEME-UHFFFAOYSA-N
  • Key: OUYCCCASQSFEME-MRVPVSSYSA-N
SMILES
  • N[C@@H](Cc1ccc(O)cc1)C(O)=O
  • Zwitterion: [NH3+][C@@H](Cc1ccc(O)cc1)C([O-])=O
Properties
Chemical formula
C9H11NO3
Molar mass 181.191 g·mol−1
Appearance white solid
Solubility in water
.0453 g/100 mL
Magnetic susceptibility (χ)
-105.3·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Supplementary data page
Tyrosine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

L-Tyrosine or tyrosine (symbol Tyr or Y)[2] or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyrós, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese.[3][4] It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine.[5] It is encoded by the codons UAC and UAU in messenger RNA.

The one-letter symbol Y was assigned to tyrosine for being alphabetically nearest of those letters available. Note that T was assigned to the structurally simpler threonine, U was avoided for its similarity with V for valine, W was assigned to tryptophan, while X was reserved for undetermined or atypical amino acids.[6] The mnemonic tYrosine was also proposed.[7]

  1. ^ a b Frey MN, Koetzle TF, Lehmann MS, Hamilton WC (1973). "Precision neutron diffraction structure determination of protein and nucleic acid components. X. A comparison between the crystal and molecular structures of L-tyrosine and L-tyrosine hydrochloride". J. Chem. Phys. 58 (6): 2547–2556. Bibcode:1973JChPh..58.2547F. doi:10.1063/1.1679537.
  2. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
  3. ^ "Tyrosine". The Columbia Electronic Encyclopedia, 6th ed. Infoplease.com — Columbia University Press. 2007. Retrieved 2008-04-20.
  4. ^ Harper D (2001). "Tyrosine". Online Etymology Dictionary. Retrieved 2008-04-20.
  5. ^ "Amino Acids - Tyrosine". www.biology.arizona.edu. Retrieved 2018-01-31.
  6. ^ "IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6.
  7. ^ Saffran M (April 1998). "Amino acid names and parlor games: from trivial names to a one-letter code, amino acid names have strained students' memories. Is a more rational nomenclature possible?". Biochemical Education. 26 (2): 116–118. doi:10.1016/S0307-4412(97)00167-2.

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Tyrosine

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L-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins...

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Tyrosine kinase

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A tyrosine kinase is an enzyme that can transfer a phosphate group from ATP to the tyrosine residues of specific proteins inside a cell. It functions...

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Receptor tyrosine kinase

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Tyrosine hydroxylase

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Tyrosine hydroxylase or tyrosine 3-monooxygenase is the enzyme responsible for catalyzing the conversion of the amino acid L-tyrosine to L-3,4-dihydroxyphenylalanine...

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Tyrosine phosphorylation

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Tyrosine phosphorylation is the addition of a phosphate (PO43−) group to the amino acid tyrosine on a protein. It is one of the main types of protein phosphorylation...

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Tyrosine decarboxylase

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The enzyme tyrosine decarboxylase (EC 4.1.1.25) catalyzes the chemical reaction L-tyrosine ⇌ {\displaystyle \rightleftharpoons } tyramine + CO2 Hence...

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Tyrosine kinase inhibitor

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A tyrosine kinase inhibitor (TKI) is a pharmaceutical drug that inhibits tyrosine kinases. Tyrosine kinases are enzymes responsible for the activation...

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Tyrosine aminotransferase

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Tyrosine aminotransferase (or tyrosine transaminase) is an enzyme present in the liver and catalyzes the conversion of tyrosine to 4-hydroxyphenylpyruvate...

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Catecholamine

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fight-or-flight response. Tyrosine is created from phenylalanine by hydroxylation by the enzyme phenylalanine hydroxylase. Tyrosine is also ingested directly...

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Philadelphia chromosome

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cluster region BCR gene of chromosome 22, coding for a hybrid protein: a tyrosine kinase signaling protein that is "always on", causing the cell to divide...

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Tyrosine hydroxylase deficiency

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Tyrosine hydroxylase deficiency (THD) is a disorder caused by disfunction of tyrosine hydroxylase, an enzyme involved in the biosynthesis of dopamine...

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Protein kinase

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groups of serines and threonines in their targets. Most of the others are tyrosine kinases, although additional types exist. Protein kinases are also found...

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Tyrosine sulfation

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In biochemistry, tyrosine sulfation is a posttranslational modification where a sulfate group (−SO3) is added to a tyrosine residue of a protein molecule...

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Phenylalanine

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biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline)...

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Tyrosinemia

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inborn, in which the body cannot effectively break down the amino acid tyrosine. Symptoms of untreated tyrosinemia include liver and kidney disturbances...

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Protein tyrosine phosphatase

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phosphorylated tyrosine residues on proteins: [a protein]-tyrosine phosphate + H2O = [a protein]-tyrosine + phosphate Protein tyrosine (pTyr) phosphorylation...

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Amino acid synthesis

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concentrations of the repressor protein and corepressor level. Phenylalanine, tyrosine, and tryptophan, the aromatic amino acids, arise from chorismate. The first...

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Amino acid

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and therefore do not have pKas, with the exception of tyrosine (Tyr, Y). The hydroxyl of tyrosine can deprotonate at high pH forming the negatively charged...

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