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Isoleucine
 
 
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Isoleucine (abbreviated as Ile or I) is an a-amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 with the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(NH2)CH(CH3)CH2CH3. It is an essential amino acid
Essential amino acid

File:BakedFish.jpgAn essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo synthesis by the organism , and therefore must be supplied in the diet....
, 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
Threonine

Threonine is an a-amino acid with the chemical formula HO2CCHCHCH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as Chemical polarity....
, isoleucine is one of two common amino acids that have a chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 side chain.






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Isoleucine (abbreviated as Ile or I) is an a-amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 with the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(NH2)CH(CH3)CH2CH3. It is an essential amino acid
Essential amino acid

File:BakedFish.jpgAn essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo synthesis by the organism , and therefore must be supplied in the diet....
, 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
Threonine

Threonine is an a-amino acid with the chemical formula HO2CCHCHCH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as Chemical polarity....
, isoleucine is one of two common amino acids that have a chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 side chain. Four stereoisomers of isoleucine are possible, including two possible diastereomer
Diastereomer

Diastereomers are stereoisomers that are not enantiomers . Diastereomers can have different physical properties and different reactivity. In another definition diastereomers are pairs of isomers that have opposite configurations at one or more of the chiral centers but are not mirror images of each other ....
s 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
Pyruvic acid

Pyruvic acid is an organic acid. It is also a ketone. It is the simplest keto acids. The carboxylate ion of pyruvic acid is known as pyruvate....
 and alpha-ketoglutarate. Enzymes involved in this biosynthesis include:
  1. Acetolactate synthase
    Acetolactate synthase

    The acetolactate synthase enzyme is a protein which in humans is encoded by the ILVBL gene. ALS catalyzes the first step in the synthesis of the branched-chain amino acids ....
     (also known as acetohydroxy acid synthase)
  2. Acetohydroxy acid isomeroreductase
  3. Dihydroxyacid dehydratase
  4. Valine aminotransferase


Isomers of isoleucine



Synthesis

Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate. Synthetic isoleucine was originally reported in 1905.

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