alpha-Aminobutyric acid

α-Aminobutyric acid

Names
IUPAC name 2-Aminobutanoic acid
Other names 2-Aminobutyric acid; α-Aminobutanoic acid; Ethylglycine
Identifiers
CAS Registry Number	2835-81-6 Y
ChEBI	CHEBI:35621 Y
ChEMBL	ChEMBL55242 Y
ChemSpider	6405 Y
InChI InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7) Y Key: QWCKQJZIFLGMSD-UHFFFAOYSA-N Y InChI=1/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7) Key: QWCKQJZIFLGMSD-UHFFFAOYAG
Jmol-3D images	Image
PubChem	6657
SMILES O=C(O)C(N)CC
UNII	8306QPJ19P Y
Properties
Chemical formula	C4H9NO2
Molar mass	103.12 g/mol
Acidity (pKa)	2.55 (carboxyl), 9.60 (amino)[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

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, γ-aminobutyric acid (GABA) and β-aminobutyric acid (BABA).

In contrast, GABA is a neurotransmitter and is not used in protein synthesis, and it is almost always referred to as "GABA".

References