3-Aminoisobutyric acid

3-Aminoisobutyric acid
Skeletal formula of 3-aminoisobutyric acid
Ball-and-stick model of the 3-aminoisobutyric acid molecule
Names
Preferred IUPAC name
3-Amino-2-methylpropanoic acid
Other names
3-Aminoisobutyrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.132 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7) checkY
    Key: QCHPKSFMDHPSNR-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
    Key: QCHPKSFMDHPSNR-UHFFFAOYAN
  • CC(CN)C(=O)O
  • O=C(O)C(C)CN
Properties
C4H9NO2
Molar mass 103.12 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

3-Aminoisobutyric acid (also known as β-aminoisobutyric acid or BAIBA) is a product formed by the catabolism of thymine.

During exercise, the increase of PGC-1α protein triggers the secretion of BAIBA from exercising muscles to blood (concentration 2 to 3 μM in human serum). When BAIBA reaches the white fat tissue, it activates the expression of thermogenic genes via PPARα receptors, resulting in a browning of white fat cells.[1] One of the consequences of the BAIBA activity is the increase of the background metabolism of the BAIBA target cells.

It is thought to play a number of roles in cell metabolism, how body burns fat and regulates insulin, triglycerides, and total cholesterol.[2][3][4]

BAIBA is found as a normal metabolite of skeletal muscle in 2014. The plasma concentrations are increased in human by exercise. The production is likely a result of enhanced mitochondrial activity as the increase is also observed in the muscle of PGC-1a overexpression mice. BAIBA is proposed as protective factor against metabolic disorder since it can induce brown fat function.[1]

See also

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References

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  1. ^ a b Roberts LD, Boström P, O'Sullivan JF, Schinzel RT, Lewis GD, Dejam A, et al. (7 January 2014). "β-Aminoisobutyric acid induces browning of white fat and hepatic β-oxidation and is inversely correlated with cardiometabolic risk factors". Cell Metabolism. 19 (1): 96–108. doi:10.1016/j.cmet.2013.12.003. PMC 4017355. PMID 24411942.
  2. ^ Begriche K, Massart J, Fromenty B (June 2010). "Effects of β-aminoisobutyric acid on leptin production and lipid homeostasis: mechanisms and possible relevance for the prevention of obesity". Fundamental & Clinical Pharmacology. 24 (3): 269–82. doi:10.1111/j.1472-8206.2009.00765.x. PMID 19735301. S2CID 2520238.
  3. ^ Ibrahim A, Neinast M, Arany ZP (June 2017). "Myobolites: muscle-derived metabolites with paracrine and systemic effects". Current Opinion in Pharmacology. 34: 15–20. doi:10.1016/j.coph.2017.03.007. PMC 5651206. PMID 28441626.
  4. ^ Tanianskii DA, Jarzebska N, Birkenfeld AL, O'Sullivan JF, Rodionov RN (February 2019). "Beta-Aminoisobutyric Acid as a Novel Regulator of Carbohydrate and Lipid Metabolism". Nutrients. 11 (3): 524. doi:10.3390/nu11030524. PMC 6470580. PMID 30823446.
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