Prephenic acid

Prephenic acid

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)^Y, 87664-40-2 (cis)^Y
PubChem	1028
ChemSpider	16735981^Y
MeSH	Prephenic+acid
Jmol-3D images	Image 1
SMILES O=C(O)[C@@]/1(CC(=O)C(O)=O)\C=C/[C@@H](O)\C=C\1
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+^Y Key: FPWMCUPFBRFMLH-XGAOUMNUSA-N^Y 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
Properties
Molecular formula	C₁₀H₁₀O₆
Molar mass	226.18 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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.