α-Aminobutyric acid

α-Aminobutyric acid
Names
	IUPAC name Homoalanine
	Systematic IUPAC name 2-Aminobutanoic acid
	Other names 2-Aminobutyric acid; α-Aminobutanoic acid; Ethylglycine;; 2-Azaniumylbutanoate
Identifiers
CAS Number	2835-81-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35621 ;
ChEMBL	ChEMBL55242 ;
ChemSpider	6405 ;
ECHA InfoCard	100.018.742
PubChem CID	6657;
UNII	8306QPJ19P ;
CompTox Dashboard (EPA)	DTXSID90862679 ;
	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)	-62.1·10−6 cm3/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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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

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