Isoleucine

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Chemical structure of Isoleucine
Chemical structure of Isoleucine
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:[2]

  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.[3] Synthetic isoleucine was originally reported in 1905.[4]

References

  1. IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved 2007-05-17. 
  2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. Marvel, C. S. “dl-Isoleucine” Organic Syntheses, Collected Volume 3, p.495 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0495.pdf
  4. Bouveault and Locquin, Compt. rend., 141, 115 (1905).

External links


<tr bgcolor="#ccccff"><td colspan="3" align="center">
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Major families of biochemicals</td></tr><tr><td colspan="3" style="text-align: center;">Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides</td></tr><tr bgcolor="pink"><td style="white-space: nowrap; width: 10%; color: pink;">Analogues of nucleic acids:</td><td align="center">The 20 Common Amino Acids ("dp" = data page)</td><td style="white-space: nowrap; width: 10%; color: pink;">Analogues of nucleic acids:</td></tr>
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:Izoleŭcinoko:이소류신 hr:Izoleucin id:Isoleusin it:Isoleucina he:איזולאוצין lv:Izoleicīns lb:Isoleucin lt:Izoleucinas nl:Isoleucinefi:Isoleusiini sv:Isoleucinuk:Ізолейцин


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