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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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.742 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)Key: QWCKQJZIFLGMSD-UHFFFAOYSA-N
  • InChI=1/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)Key: QWCKQJZIFLGMSD-UHFFFAOYAG
SMILES
  • O=C(O)C(N)CC
Properties
Chemical formula 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)
Magnetic susceptibility (χ) -62.1·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. Bibcode:1997Sci...275..951C. doi:10.1126/science.275.5302.951. PMID 9020072. S2CID 10979716.
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