alpha-Ketobutyric acid

α-Ketobutyric acid
Names


IUPAC name 2-oxobutanoic acid
Identifiers
CAS Number	600-18-0^Y
ChEBI	CHEBI:30831^Y
ChEMBL	ChEMBL171246^Y
ChemSpider	57^Y
DrugBank	DB04553^Y
Jmol interactive 3D	Image
KEGG	C00109^Y
MeSH	Alpha-ketobutyric+acid
PubChem	58
InChI InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)^Y Key: TYEYBOSBBBHJIV-UHFFFAOYSA-N^Y InChI=1/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) Key: TYEYBOSBBBHJIV-UHFFFAOYAT
SMILES O=C(C(=O)O)CC
Properties
Chemical formula	C₄H₆O₃
Molar mass	102.089 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

α-Ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine, produced by the catabolism of the amino acid by threonine dehydratase. It is also produced by the degradation of homocysteine and the metabolism of methionine.

α-Ketobutyric acid is transported into the mitochondrial matrix, where it is converted to propionyl-CoA by Branched-chain alpha-keto acid dehydrogenase complex. Further mitochondrial reactions produce succinyl CoA. This is first through the enzyme mitochondria Propionyl-CoA carboxylase with biotin as a cofactor to produce S-methylmalonyl-CoA. This is subsequently converted to R-methylmalonyl-CoA by mitochondrial methylmalonyl-CoA epimerase. Finally, mitochondrial methylmalonyl-CoA mutase with cofactor adenosylcobalamin produces succinyl-CoA which enters the citric acid cycle.^[1]

Conversion in sotolon in French vin jaune

Vin jaune is marked by the formation of sotolon from alpha-ketobutyric acid.^[2]^[3]

References

↑ http://smpdb.ca/
↑ Pham TT, Guichard E, Schlich P, Charpentier C; Elisabeth; Pascal; Claudine (1995). "Optimal Conditions for the Formation of Sotolon from α-Ketobutyric Acid in the French 'Vin Jaune'". Journal of Agricultural and Food Chemistry 43 (10): 2616–2619. doi:10.1021/jf00058a012.
↑ Guichard E, Pham TT, Etievant P; Pham; Etievant (1993). "Quantitative Determination of Sotolon in Wines by High-Performance Liquid Chromatography". Chromatographia 37 (9–10): 539–542. doi:10.1007/BF02275793.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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alpha-Ketobutyric acid

Conversion in sotolon in French vin jaune

See also

References