Prephenic acid

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Prephenic acid
Identifiers
CAS number [126-49-8]
PubChem 1028
MeSH Prephenic+acid
SMILES C1=CC(C=CC1O)(CC(=O)C(=O)O)C(=O)O
Properties
Molecular formula C10H10O6
Molar mass 226.183
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Prephenic acid, more commonly 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]

[edit] References

  1. ^ Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry: 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. 
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