Chemistry:α-Aminobutyric acid

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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
Homoalanine
Systematic IUPAC name
2-Aminobutanoic acid
Other names
2-Aminobutyric acid; α-Aminobutanoic acid; Ethylglycine;
2-Azaniumylbutanoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
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]

References

  1. Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. Cronin, John R.; Pizzarello, Sandra (1997). "Enantiomeric Excesses in Meteoritic Amino Acids". Science 275 (5302): 951–955. doi:10.1126/science.275.5302.951. PMID 9020072. Bibcode1997Sci...275..951C.