L(+)-2-Aminobutyric acid Chemical Properties

Melting point:

300 °C

alpha 

21.6 º (c=2, 5N HCl)

Boiling point:

215.2±23.0 °C(Predicted)

Density 

1.2300 (estimate)

refractive index 

1.4650 (estimate)

storage temp. 

room temp

solubility 

22.7 g/100 mL (22°C)

pka

2.29(at 25℃)

form 

Crystalline Powder

color 

White to beige

biological source

Porcine kidney
microbial
plant

Water Solubility 

22.7 g/100 mL (22 ºC)

Merck 

14,428

BRN 

1720935

InChIKey

QWCKQJZIFLGMSD-VKHMYHEASA-N

CAS DataBase Reference

1492-24-6(CAS DataBase Reference)

NIST Chemistry Reference

(l)-2-Aminobutanoic acid(1492-24-6)

EPA Substance Registry System

Butanoic acid, 2-amino-, (2S)- (1492-24-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29224999

MSDS

• Language:English Provider:L-2-Aminobutanoic acid
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L(+)-2-Aminobutyric acid Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

aminobutyric acid is an amino acid with water-binding properties and possible anti-inflammatory capacities.

Uses

L-(+)-2-Aminobutyric acid is used in the biosynthesis of nonribosomal peptides. It acts as a receptor antagonist. It is also used as a chiral reagent. Further, it is used in the determination of substrate of glutamyl cysteine acid synthase. In addition to this, it is also utilized as a drug intermediate.

Definition

ChEBI: An optically active form of alpha-aminobutyric acid having L-configuration.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 450, 1946 DOI: 10.1021/ja01207a032

General Description

L-2-Aminobutyric acid is synthesized from L-threonine and L-aspartic acid through a ?-transamination reaction. It is an L-alanine analogue with an ethyl side chain.

Biochem/physiol Actions

L-α-Aminobutyric acid (AABA) is an isomer of the non-natural amino acid aminobutyric acid with activity in the γ-glutamyl cycle that regulates glutathione biosynthesis. Recently AABA has been studied as a supplement to in vitro maturation medium (NCSU 23 medium) for culture of oozytes and embryos. This product has been qualified for use in cell culture. AABA is also used as a substitute amino acid for alanine in studies on peptide function.

Synthesis

The preparation of l-2-aminobutyric acid (l-ABA) is mainly achieved by chemical synthesis or enzymatic conversion. In chemical methods, synthesis of l-ABA has been extensively reported, including ammonolysis of α-halogen acid, reduction reaction, ammoniation hydrolysis reaction and butanone acid reduction. However, the obvious disadvantages of chemical synthesis, such as poor selectivity, harsh reaction conditions, various byproducts, and the difficulty in separation and purification, limited its development. It is reported that l-ABA was synthesized in a transamination reaction from α-ketobutyric acid and l-aspartic acid as substrates using aromatic aminotransferase or produced from α-ketobutyric acid and benzylamine using ω-aminotransferase. l-ABA could also be produced from the reduction of α-keto acids with l-leucine dehydrogenase or glutamate dehydrogenase[1].

Purification Methods

Crystallise butyrine from aqueous EtOH, and the melting point depends on heating rate but has m 303o in a sealed tube. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2399 IR: 2401 1961, Beilstein 4 III 1294, 4 IV 2584.]

References

[1] Xu, Jian-Miao et al. “Fermentative production of the unnatural amino acid L-2-aminobutyric acid based on metabolic engineering.” Microbial cell factories vol. 18,1 43. 28 Feb. 2019, doi:10.1186/s12934-019-1095-z.

L(+)-2-Aminobutyric acid(1492-24-6)Related Product Information

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