Prephenic acid

Prephenic acid

Names
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
CAS Number	126-49-8 (unspecified) 87664-40-2 (cis)
ChEBI	CHEBI:84387
ChemSpider	16735981
Jmol interactive 3D	Image
MeSH	Prephenic+acid
PubChem	1028
InChI InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+ Key: FPWMCUPFBRFMLH-XGAOUMNUSA-N InChI=1/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+ Key: FPWMCUPFBRFMLH-XGAOUMNUBN
SMILES O=C(O)[C@@]/1(CC(=O)C(O)=O)\C=C/[C@@H](O)\C=C\1
Properties
Chemical formula	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).
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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

1. Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry 17 (18): 3700. doi:10.1021/bi00611a004.
2. 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.