Isoleucine
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219106891
2008-06-13T16:28:34Z
DumZiBoT
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robot Modifying: [[id:Isoleusin]]
{{Chembox new
| ImageFile = Isoleucin - Isoleucine.svg
<!-- | ImageSize = 200px -->
| ImageName = Chemical structure of Isoleucine
| ImageFile1 = L-isoleucine-3D-sticks2.png
<!-- | ImageSize1 = 175px -->
| ImageName1 = Chemical structure of Isoleucine
| Name = (2''S'',3''S'')-2-amino-3-methylpentanoic acid
| Section1 = {{Chembox Identifiers
| PubChem = 791
| SMILES = CC[C@H](C)[C@H](N)C(O)=O
}}
| Section2 = {{Chembox Properties
| C =6 | H =13 | N =1 | O=2
| MolarMass = 131.18 g/mol
}}
}}
'''Isoleucine''' (abbreviated as '''Ile''' or '''I''')<ref>{{cite web | author=IUPAC-IUBMB Joint Commission on Biochemical Nomenclature | title=Nomenclature and Symbolism for Amino Acids and Peptides | work=Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc | url=http://www.chem.qmul.ac.uk/iupac/AminoAcid/ | accessdate=2007-05-17}}</ref> is an α-[[amino acid]] with the [[chemical formula]] HO<sub>2</sub>CCH(NH<sub>2</sub>)CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub>. It is an [[essential amino acid]], which means that humans cannot synthesize it, so it must be part of our diet. Its codons are AUU, AUC and AUA.
With a hydrocarbon side chain, isoleucine is classified as a [[hydrophobic]] amino acid. Together with [[threonine]], isoleucine is one of two common amino acids that have a [[Chirality (chemistry)|chiral]] side chain. Four [[stereoisomer]]s of isoleucine are possible, including two possible [[diastereomer]]s of <small>L</small>-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2''S'',3''S'')-2-amino-3-methylpentanoic acid.
== Biosynthesis ==
As an essential amino acid, isoleucine is not synthesized in animals, hence it must be ingested, usually as a component of proteins. In plants and microorganisms, it is synthesized via several steps, starting from [[pyruvic acid]] and [[alpha-ketoglutarate]]. Enzymes involved in this biosynthesis include:<ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.</ref>
# [[Acetolactate synthase]] (also known as acetohydroxy acid synthase)
# [[Acetohydroxy acid isomeroreductase]]
# [[Dihydroxyacid dehydratase]]
# [[Valine aminotransferase]]
==Isomers of isoleucine==
{| border="1" cellspacing="0" cellpadding="3" style="font-size:x-small; margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} colspan=8| '''Forms of Isoleucine'''
|-
|style="background-color:#F3F3F3;"|'''[[Common name]]''': || isoleucine || D-isoleucine || L-isoleucine || DL-isoleucine || allo-D-isoleucine || allo-L-isoleucine || allo-DL-isoleucine
|-
|style="background-color:#F3F3F3;"|'''Synonyms''': || || (R)-Isoleucine || L(+)-Isoleucine || (R*,R*)-isoleucine || || alloisoleucine ||
|-
|style="background-color:#F3F3F3;"|'''[[PubChem]]''':||{{PubChemCID|791}}||{{PubChemCID|94206}} ||{{PubChemCID|6306}} ||{{PubChemCID|76551}} || || ||
|-
|style="background-color:#F3F3F3;"|'''[[EINECS number]]''':||{{EINECS|207-139-8}}||{{EINECS|206-269-2}}||{{EINECS|200-798-2}}||||{{EINECS|216-143-9}}||{{EINECS|216-142-3}}||{{EINECS|221-464-2}}
|-
|style="background-color:#F3F3F3;"|'''[[CAS number]]''':||443-79-8
| 319-78-8
| 73-32-5
|
| 1509-35-9
| 1509-34-8
| 3107-04-8
|}
==Synthesis==
Isoleucine can be synthesized in a multistep procedure starting from [[2-bromobutane]] and [[diethylmalonate]].<ref>{{OrgSynth | Marvel, C. S. | title = dl-Isoleucine | collvol = 3 | collvolpages = 495 | year = 1955 | prep = cv3p0495}}</ref> Synthetic isoleucine was originally reported in 1905.<ref>Bouveault and Locquin, Compt. rend., 141, 115 (1905).</ref>
==References==
<references/>
==External links==
* [http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/IleVal.html Isoleucine and valine biosynthesis]
* [http://www.compchemwiki.org/index.php?title=Isoleucine Computational Chemistry Wiki]
{{AminoAcids}}
[[Category:Proteinogenic amino acids]]
[[Category:Glucogenic amino acids]]
[[Category:Ketogenic amino acids]]
[[Category:Branched-chain amino acids]]
[[Category:Essential amino acids]]
[[ca:Isoleucina]]
[[cs:Isoleucin]]
[[da:Isoleucin]]
[[de:Isoleucin]]
[[es:Isoleucina]]
[[eo:Izoleŭcino]]
[[fr:Isoleucine]]
[[ko:이소류신]]
[[hr:Izoleucin]]
[[id:Isoleusin]]
[[it:Isoleucina]]
[[he:איזולאוצין]]
[[lv:Izoleicīns]]
[[lb:Isoleucin]]
[[lt:Izoleucinas]]
[[nl:Isoleucine]]
[[ja:イソロイシン]]
[[pl:Izoleucyna]]
[[pt:Isoleucina]]
[[ru:Изолейцин]]
[[sk:Izoleucín]]
[[fi:Isoleusiini]]
[[sv:Isoleucin]]
[[tr:İzolösin]]
[[uk:Ізолейцин]]
[[vls:Isoleucine]]
[[zh:異亮氨酸]]