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Isoleucine
From Wikipedia, the free encyclopedia
  Chemical structure of L-isoleucine |
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Isoleucine |
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| 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.
Contents |
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:[2]
- Acetolactate synthase
- Acetohydroxy acid isomeroreductase
- Dihydroxyacid dehydratase
- Valine aminotransferase
| 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: | CID 791 | CID 94206 | CID 6306 | CID 76551 | |||
| EINECS number: | 207-139-8 | 206-269-2 | 200-798-2 | 216-143-9 | 216-142-3 | 221-464-2 | |
| CAS number: | 443-79-8 | 319-78-8 | 73-32-5 | 1509-35-9 | 1509-34-8 | 3107-04-8 | |
Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate.[3] Synthetic isoleucine was originally reported in 1905.[4]
- ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
- ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
- ^ Marvel, C. S. “dl-Isoleucine” Organic Syntheses, Collected Volume 3, p.495 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0495.pdf
- ^ Bouveault and Locquin, Compt. rend., 141, 115 (1905).
| 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) | ||