Prephenic acid

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Prephenic acid
Prephenic acid.svg
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
126-49-8 (unspecified) N
87664-40-2 (cis) YesY
ChEBI CHEBI:84387 N
ChemSpider 16735981 YesY
Jmol-3D images Image
MeSH Prephenic+acid
PubChem 1028
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).
 N verify (what isYesY/N?)
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]

Prephenate biosynthesis.png

References[edit]

  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.