Isoleucine
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| 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]
- Acetolactate synthase
- Acetohydroxy acid isomeroreductase
- Dihydroxyacid dehydratase
- 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
| Major families of biochemicals | ||
| Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides | ||
| 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) | ||
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
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

