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Names | |
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IUPAC name
Homoalanine
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Systematic IUPAC name
2-Aminobutanoic acid | |
Other names
2-Aminobutyric acid; α-Aminobutanoic acid; Ethylglycine;
2-Azaniumylbutanoate | |
Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.018.742 |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C4H9NO2 | |
Molar mass | 103.12 g/mol |
Appearance | white solid |
Melting point | 305 °C (581 °F; 578 K) |
Acidity (pKa) | 2.55 (carboxyl), 9.60 (amino) [1] |
-62.1·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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-.
Homoalanine 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 one of the three isomers of aminobutyric acid. The two other are the neurotransmitter γ-Aminobutyric acid (GABA) and β-Aminobutyric acid (BABA) which is known for inducing plant disease resistance.
The conjugate base of α-aminobutyric acid is the carboxylate α-aminobutyrate.
This amino acid has been detected in meteorites. [2]