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Encyclopedia > Isoleucine
Chemical structure of Isoleucine Chemical structure of Isoleucine
Chemical structure of L-isoleucine

Isoleucine Image File history File links Download high resolution version (1396x1476, 21 KB) Licensing File links The following pages link to this file: Amino acid Isoleucine User:Benjah-bmm27/Gallery ... Image File history File links Size of this preview: 427 × 599 pixelsFull resolution (722 × 1013 pixel, file size: 46 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ...

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 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 synthesize it, so it must be part of our diet. With a hydrocarbon side chain, Isoleucine is classified as a hydrophobic amino acid. IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... PubChem is a database of chemical molecules. ... This article or section does not cite any references or sources. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... This article does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Physical properties Hazard properties Chemical properties Pharmacological properties OrganicBox_complete References a  b  c  d  e  f  g  PubChem 6306 ... Phenylalanine is one of the standard amino acids. ... This article or section does not cite any references or sources. ... An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ...


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. Threonine is one of the 20 natural amino acids. ... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ... Diastereomers (or diastereoisomers) are stereoisomers that are not enantiomers (mirror images of each other). ...

Contents

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] Pyruvic acid (CH3COCO2H) is an alpha-keto acid which plays an important role in biochemical processes. ... Ketoglutaric acid is refers to either of two crystalline ketone derivatives of glutaric acid which differ only by the position of the ketone functional group. ...

  1. acetolactate synthase
  2. acetohydroxy acid isomeroreductase
  3. dihydroxyacid dehydratase
  4. valine aminotransferase

The acetolactate synthase (ALS) enzyme (also known as acetohydroxyacid synthase, or AHAS) is the first step in the synthesis of the branched-chain amino acids (valine, leucine, and isoleucine). ... A reductase is an enzyme which lowers the activation energy for a reduction reaction. ... Dehydratase is an enzyme that catalyzes the removal of oxygen and hydrogen from organic compounds in the form of water. ... Valine is an amino acid that cannot be synthesized by humans, so it is considered an essential amino acid for human life. ...

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

In science, a common name is any name by which a species or other concept is known that is not the official scientific name. ... PubChem is a database of chemical molecules. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ...

Synthesis

Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate.[2] Synthetic isoleucine was originally reported in 1905.[3] Tetrafluoroethane (a haloalkane) is a clear liquid which boils well below room temperature (as seen here) and can be extracted from common canned air canisters by simply inverting them during use. ...


References

  1. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  2. ^ Marvel, C. S. “dl-Isoleucine” Organic Syntheses, Collected Volume 3, p.495 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0495.pdf
  3. ^ Bouveault and Locquin, Compt. rend., 141, 115 (1905).

External links

  • Isoleucine and valine biosynthesis
  • Computational Chemistry Wiki



v • d • e
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | 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)

  Results from FactBites:
 
BioCarta - Charting Pathways of Life (178 words)
Isoleucine is an essential amino acid, only synthesized in plants and bacteria, and required in the diet by animals.
The isoleucine pathway is almost the same as the valine biosynthesis pathway, using the same enzymes, and varying primarily at the first step in the pathway.
As a key enzyme in the synthesis of leucine, isoleucine and valine, acetolactate synthase is the target of several herbicides and mutation of this enzyme is responsible in some cases for the development of herbicide resistance.
  More results at FactBites »


 

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