Isoleucine

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Image:Isoleucin - Isoleucine.svg Image:L-isoleucine-3D-sticks2.png Chemical structure of L-isoleucine
Isoleucine
Systematic (IUPAC) name
(2S,3S)-2-amino-3-methylpentanoic acid
Identifiers
CAS number	73-32-5
PubChem	791
Chemical data
Formula	C6H13NO2
Molar mass	131.18 g/mol
SMILES	CC[C@H](C)[C@H](N)C(O)=O
Complete data

Isoleucine (abbreviated as Ile or I)^[1] is an α-amino acid with the chemical formula HO₂CCH(NH₂)CH(CH₃)CH₂CH₃. 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 chiral side chain. Four stereoisomers of isoleucine are possible, including two possible diastereomers of L-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2S,3S)-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:^[1]

1. Acetolactate synthase
2. Acetohydroxy acid isomeroreductase
3. Dihydroxyacid dehydratase
4. Valine aminotransferase

Isomers of isoleucine

Forms of Isoleucine
Common name:	isoleucine	D-isoleucine	L-isoleucine	DL-isoleucine	allo-D-isoleucine	allo-L-isoleucine	allo-DL-isoleucine
Synonyms:		(R)-Isoleucine	L(+)-Isoleucine	(R*,R*)-isoleucine		alloisoleucine
PubChem:	Template:PubChemCID	Template:PubChemCID	Template:PubChemCID	Template:PubChemCID
EINECS number:	Template:EINECS	Template:EINECS	Template:EINECS		Template:EINECS	Template:EINECS	Template:EINECS
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.^[1] Synthetic isoleucine was originally reported in 1905.^[1]

References

External links

• Isoleucine and valine biosynthesis
• Computational Chemistry Wiki

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Analogues of nucleic acids:	The 20 Common Amino Acids ("dp" = data page)	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)

ca:Isoleucina

da:Isoleucin de:Isoleucineo: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fi:Isoleusiini sv:Isoleucinuk:Ізолейцин