4-Hydroxyphenylpyruvic acid
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Preferred IUPAC name 3-(4-Hydroxyphenyl)-2-oxopropanoic acid | |
Other names 4-Hydroxyphenylpyruvate p-Hydroxyphenylpyruvic acid p-Hydroxyphenylpyruvate | |
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ECHA InfoCard | 100.005.322 |
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Chemical formula | C9H8O4 |
Molar mass | 180.157 g/mol |
Melting point | 219-220°C[1] |
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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 |
Chemical compound
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.[2] Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.[3]
It is an intermediary compound in the biosynthesis of scytonemin.
See also
References
- ^ a b "4-Hydroxyphenylpyruvic acid".
- ^ Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal. 142 (2): 231–45. doi:10.1042/bj1420231. 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. doi:10.1128/jb.176.17.5312-5319.1994. PMC 196716. PMID 8071207.
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