4-Hydroxyphenylpyruvic acid

4-Hydroxyphenylpyruvic acid
Names

IUPAC name 3-(4-hydroxyphenyl)-2-oxo-propanoic acid
Other names 4-Hydroxyphenylpyruvate p-Hydroxyphenylpyruvic acid p-Hydroxyphenylpyruvate
Identifiers
CAS Number	156-39-8^N
ChEBI	CHEBI:15999^Y
ChEMBL	ChEMBL607712^Y
ChemSpider	954^Y
DrugBank	DB07718^Y
IUPHAR/BPS	6629
Jmol interactive 3D	Image
KEGG	C01179^Y
PubChem	979
InChI InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)^Y Key: KKADPXVIOXHVKN-UHFFFAOYSA-N^Y InChI=1/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) Key: KKADPXVIOXHVKN-UHFFFAOYAH
SMILES O=C(O)C(=O)Cc1ccc(O)cc1
Properties
Chemical formula	C₉H₈O₄
Molar mass	180.157 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 ^YN ?)
Infobox references

4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyrosine to 4-HPPA is in turn catalyzed by tyrosine aminotransferase.^[1] Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.^[2]

It is an intermediary compound in the biosynthesis of scytonemin.

References

↑ Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal 142 (2): 231–45. PMC 1168273. PMID 4155291.
↑ Denoya, Claudio; Skinner, Deborah; Morgenstern, Margaret (September 1994). "A Streptomyces avermitilis gene encoding a 4-hydroxyphenylpyruvic acid dioxygenase-like protein that directs the production of homogentisic acid and an ochronotic pigment in Escherichia coli". Journal of Bacteriology 1 (17): 5312–5319. Retrieved 18 July 2011.

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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4-Hydroxyphenylpyruvic acid

See also

References