Prephenic acid
Names | |
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IUPAC name
1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-dienecarboxylic acid | |
Other names
Prephenate; cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid | |
Identifiers | |
126-49-8 (unspecified) 87664-40-2 (cis) | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:84387 |
ChemSpider | 16735981 |
MeSH | Prephenic+acid |
PubChem | 1028 |
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Properties | |
C10H10O6 | |
Molar mass | 226.18 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.
It is synthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate.[1][2]
References
- ↑ Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700. doi:10.1021/bi00611a004.
- ↑ Peter Kast, Yadu B. Tewari, Olaf Wiest, Donald Hilvert, Kendall N. Houk, and Robert N. Goldberg (1997). "Thermodynamics of the Conversion of Chorismate to Prephenate: Experimental Results and Theoretical Predictions". J. Phys. Chem. B. 101 (50): 10976–10982. doi:10.1021/jp972501l.
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