Chemistry:4-Hydroxyphenylpyruvic acid

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4-Hydroxyphenylpyruvic acid
4-hydroxyphenylpyruvic acid.svg
Names
Preferred IUPAC name
3-(4-Hydroxyphenyl)-2-oxopropanoic acid
Other names
4-Hydroxyphenylpyruvate
p-Hydroxyphenylpyruvic acid
p-Hydroxyphenylpyruvate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
Properties
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).
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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.

See also

References

  1. Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal 142 (2): 231–45. PMID 4155291. 
  2. 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.