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Tyrosine

Tyrosine
Skeletal formula of the L-isomer
L-Tyrosine
TYROSINE1.png
L-Tyrosine at physiological pH
Names
IUPAC name
(S)-Tyrosine
Other names
L-2-Amino-3-(4-hydroxyphenyl)propanoic acid
Identifiers
60-18-4 (L) YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:58315 N
ChEMBL ChEMBL925 YesY
ChemSpider 5833 YesY
DrugBank DB03839 N
ECHA InfoCard 100.000.419
4791
PubChem 1153
UNII 42HK56048U N
Properties
C9H11NO3
Molar mass 181.19 g·mol−1
-105.3·10−6 cm3/mol
Hazards
Safety data sheet See: data page
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Tyrosine (Tyr or Y) 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. Its codons are UAC and UAU. The word "tyrosine" is 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. It is called tyrosyl when referred to as a functional group or side chain. Tyrosine is a hydrophilic amino acid and is significantly more soluble in water than its precursor, phenylalanine, due to the thermodynamic favorability of the hydrogen bonding between the hydroxyl group of one molecule of tyrosine and the carboxyl group of another.

Aside from being a proteinogenic amino acid, tyrosine has a special role by virtue of the phenol functionality. It occurs in proteins that are part of signal transduction processes. It functions as a receiver of phosphate groups that are transferred by way of protein kinases (so-called receptor tyrosine kinases). Phosphorylation of the hydroxyl group changes the activity of the target protein.

A tyrosine residue also plays an important role in photosynthesis. In chloroplasts (photosystem II), it acts as an electron donor in the reduction of oxidized chlorophyll. In this process, it loses the hydrogen atom of its phenolic OH-group. This radical is subsequently reduced in the photosystem II by the four core manganese clusters.


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Wikipedia

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