Prephenic acid information

Prephenic acid
Names
	Preferred IUPAC name (1s,4s)-1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic 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 (unspecified);
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). verify (what is ?) 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]

^ Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700–3705. doi:10.1021/bi00611a004. PMID 100134.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1] Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700–3705. doi:10.1021/bi00611a004. PMID 100134.

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Prephenic acid information

and 8 Related for: Prephenic acid information

Prephenic acid

Shikimate pathway

Shikimic acid

Squonk

EPSP synthase

C10H10O6

Prephenate dehydratase

Chorismate synthase

Names


Preferred IUPAC name (1s,4s)-1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic 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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:84387^N
ChemSpider	16735981^Y
MeSH	Prephenic+acid
PubChem CID	1028 (unspecified)
UNII	Z66B98Z97I (unspecified)^Y
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+^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
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). N verify (what is ^YN ?) Infobox references