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Alpha-Aminobutyric acid

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Title: Alpha-Aminobutyric acid  
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Alpha-Aminobutyric acid

α-Aminobutyric acid
Skeletal formula of α-aminobutanoic acid
Ball-and-stick model of the α-aminobutanoic acid molecule as a zwitterion
Names
IUPAC name
2-Aminobutanoic acid
Other names
2-Aminobutyric acid; α-Aminobutanoic acid; Ethylglycine
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
PubChem
UNII  Y
Properties
C4H9NO2
Molar mass 103.12 g/mol
Acidity (pKa) 2.55 (carboxyl), 9.60 (amino)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

α-Aminobutyric acid (AABA), also known as homoalanine in biochemistry, is a non-proteinogenic alpha amino acid with chemical formula C4H9NO2. The straight two carbon side chain is one carbon longer than alanine, hence the prefix homo-.

Homoalaine is biosynthesised by transaminating oxobutyrate, a metabolite in isoleucine biosynthesis. It is used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing homoalanine is ophthalmic acid, which was first isolated from calf lens.

α-Aminobutyric acid is an isomer of the amino acid aminobutyric acid. It has two other isomers, the neurotransmitter γ-Aminobutyric acid (GABA) and β-Aminobutyric acid (BABA) which is known for inducing plant disease resistance.

References

  1. ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
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