Isoleucine 63543 219106891 2008-06-13T16:28:34Z DumZiBoT 6085301 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]]