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) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:84387 ;
ChemSpider	16735981 ;
MeSH	Prephenic+acid
PubChem CID	1028;
UNII	Z66B98Z97I (unspecified) ;
CompTox Dashboard (EPA)	DTXSID60894109 ;
	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	226.184 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, as well as of a large number of secondary metabolites of the shikimate pathway.

It is biosynthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate.[1][2]

Stereochemistry

Prephenic acid is an example of achiral (optically inactive) molecule which has two pseudoasymmetric atoms (i.e. stereogenic but not chirotopic centers), the C1 and the C4 cyclohexadiene ring atoms. It has been shown[3] that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s, 4s) according to the new IUPAC stereochemistry rules (2013).[4]

The other stereoisomer, i.e. trans or, better, (1r, 4r), is called epiprephenic.

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References

Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700–3705. 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.CS1 maint: multiple names: authors list (link)
Danishefsky, Samuel; Hirama, Masahiro; Fritsch, Nancy; Clardy, Jon (1979-11-01). "Synthesis of disodium prephenate and disodium epiprephenate. Stereochemistry of prephenic acid and an observation on the base-catalyzed rearrangement of prephenic acid to p-hydroxyphenyllactic acid". Journal of the American Chemical Society. 101 (23): 7013–7018. doi:10.1021/ja00517a039. ISSN 0002-7863.
Favre, Henri A; Powell, Warren H (2013-12-17). Nomenclature of Organic Chemistry. doi:10.1039/9781849733069. ISBN 9780854041824.

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[1] Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700–3705. 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.CS1 maint: multiple names: authors list (link)

[3] Danishefsky, Samuel; Hirama, Masahiro; Fritsch, Nancy; Clardy, Jon (1979-11-01). "Synthesis of disodium prephenate and disodium epiprephenate. Stereochemistry of prephenic acid and an observation on the base-catalyzed rearrangement of prephenic acid to p-hydroxyphenyllactic acid". Journal of the American Chemical Society. 101 (23): 7013–7018. doi:10.1021/ja00517a039. ISSN 0002-7863.

[4] Favre, Henri A; Powell, Warren H (2013-12-17). Nomenclature of Organic Chemistry. doi:10.1039/9781849733069. ISBN 9780854041824.

Prephenic acid

Stereochemistry

See also

References