Α-Ketobutyric acid: Difference between revisions

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Revision as of 08:47, 21 April 2012

α-Ketobutyric acid
Names


IUPAC name 2-oxobutanoic acid
Identifiers
CAS Number	600-18-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30831
ChEMBL	ChEMBL171246
ChemSpider	57
DrugBank	DB04553
ECHA InfoCard	100.009.080
KEGG	C00109
MeSH	Alpha-ketobutyric+acid
PubChem CID	58
CompTox Dashboard (EPA)	DTXSID9060524
InChI InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)Key: TYEYBOSBBBHJIV-UHFFFAOYSA-N 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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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 Adenosylcoalbamin produces succinyl-CoA which enters the citric acid cycle.

Conversion in sotolon in French Vin jaune

Vin jaune is marked by the formation of sotolon from alpha-ketobutyric acid.

References

http://pathman.smpdb.ca/pathways/SMP00452/pathway?level=2
Optimal Conditions for the Formation of Sotolon from .alpha.-Ketobutyric Acid in the French "Vin Jaune". Pham Thu Thuy, Guichard Elisabeth, Schlich Pascal and Charpentier Claudine, J. Agric. Food Chem., 1995, 43 (10), pages 2616–2619, doi:10.1021/jf00058a012
Quantitative determination of sotolon in wines by high-performance liquid chromatography. E. Guichard, T. T. Pham and P. Etievant, Chromatographia, Volume 37, Numbers 9-10, pages 539-542, doi:10.1007/BF02275793

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-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

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 Citrulline 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 α-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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Revision as of 08:47, 21 April 2012

Conversion in sotolon in French Vin jaune

See also

References