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Information about Isoleucine



Chemical structure of L-isoleucine

Isoleucine

Systematic (IUPAC) name
(2S,3S)-2-amino-3-methylpentanoic acid
Identifiers
CAS number73-32-5
PubChem        791
Chemical data
FormulaC6H13NO2 
Mol. weight131.18 g/mol
SMILESCC[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:isoleucineD-isoleucineL-isoleucineDL-isoleucineallo-D-isoleucineallo-L-isoleucineallo-DL-isoleucine
Synonyms:(R)-IsoleucineL(+)-Isoleucine(R*,R*)-isoleucinealloisoleucine
PubChem:CID 791CID 94206CID 6306CID 76551
EINECS number:207-139-8206-269-2200-798-2216-143-9216-142-3221-464-2
CAS number:443-79-8319-78-873-32-51509-35-91509-34-83107-04-8

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 on 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). [1]
4. ^ Bouveault and Locquin, Compt. rend., 141, 115 (1905).

External links


 •  • [ 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 AcidsAnalogues 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)
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
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1, −1
(amphoteric oxide)
Electronegativity 2.20 (Pauling scale) More

Atomic radius 25 pm
Atomic radius (calc.) 53 pm
Covalent radius 37 pm
Van der Waals radius 120 pm
Miscellaneous

Thermal conductivity (300 K) 180.
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1

Atomic radius 60 pm
Atomic radius (calc.
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molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12).
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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The complete data for Isoleucine

General information

Chemical formula: C

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amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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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.

Essentiality vs.


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hydrophobicity (from the combining form of water in Attic Greek hydro- and for fear phobos) refers to the physical property of a molecule (known as a hydrophobe) that is repelled from a mass of water [1].
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Threonine (abbreviated as Thr or T)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(OH)CH3. Its codons are ACU and ACA. This essential amino acid is classified as polar.
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The term chiral (pronounced /ˈkaɪɹ(ə)l̩/) is used to describe an object that is non-superimposable on its mirror image. In terms of chemistry, such objects are usually molecules.
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Stereoisomers are isomeric molecules whose atomic connectivity is the same but whose atomic arrangement in space is different.

Enantiomers

Main article: enantiomer

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Diastereomers (or diastereoisomers) are stereoisomers that are not enantiomers (mirror images of each other). Diastereomers can have different physical properties and different reactivity.
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Pyruvic acid (CH3COCO2H) is an alpha-keto acid which plays an important role in biochemical processes. The carboxylate anion of pyruvic acid is known as pyruvate.

Chemistry

Pyruvic acid is a colorless liquid with a smell similar to acetic acid.
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Alpha-ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term "ketoglutaric acid," when not further qualified, almost always refers to the alpha variant.
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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).
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A reductase is an enzyme which lowers the activation energy for a reduction reaction. [1][2]

Examples

  • 5-alpha reductase
  • Dihydrofolate reductase
  • HMG-CoA reductase
  • Methemoglobin reductase
  • Ribonucleotide reductase

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Dehydratase is an enzyme that catalyzes the removal of oxygen and hydrogen from organic compounds in the form of water. This process is also known as dehydration.

External links

  • MeSH Dehydratases

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Valine (abbreviated as Val or V)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteogenic amino acids. Its codons are GUU, GUC, GUA, and GUG.
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See also Wikipedia:Naming conventions (common names) and Wikipedia:Naming conventions
In science, a common name is any name by which a species or other concept is known that is not the official scientific name.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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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.
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide.
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