Difference between revisions of "Isoleucine" - New World Encyclopedia
({{Contracted}}) |
|||
| Line 1: | Line 1: | ||
| − | {{Claimed}} | + | {{Claimed}}{{Contracted}} |
{{OrganicBox small | {{OrganicBox small | ||
| cat=ne | | cat=ne | ||
Revision as of 20:00, 15 June 2007
  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 |
| Mol. weight | 131.18 |
| SMILES | CC[C@H](C)[C@H](N)C(O)=O |
| Complete data | |
Isoleucine is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3. Its three letter code is ILE and its one letter code is I. It is an essential amino acid, which means that humans cannot synthesise it, so it must be part of our diet. 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 has 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: | 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 | |
Synthesis
Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate.[2] Synthetic isoleucine was originally reported in 1905.[3]
Dietary aspects
Rich sources of isoleucine are eggs, chicken, pork, mutton, pulses, soya beans, cottage cheese, milk, piyal seeds, cashew nuts, and cereal grains.
ReferencesISBN links support NWE through referral fees
- ↑ 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).
External links
Template:ChemicalSources
| 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 | 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) | ||
Credits
New World Encyclopedia writers and editors rewrote and completed the Wikipedia article in accordance with New World Encyclopedia standards. This article abides by terms of the Creative Commons CC-by-sa 3.0 License (CC-by-sa), which may be used and disseminated with proper attribution. Credit is due under the terms of this license that can reference both the New World Encyclopedia contributors and the selfless volunteer contributors of the Wikimedia Foundation. To cite this article click here for a list of acceptable citing formats.The history of earlier contributions by wikipedians is accessible to researchers here:
The history of this article since it was imported to New World Encyclopedia:
Note: Some restrictions may apply to use of individual images which are separately licensed.
