3-Dehydroquinic acid

3-Dehydroquinic acid
IUPAC name (1R,3R,4S)-1,3,4-trihydroxy- 5-oxocyclohexanecarboxylic acid
Identifiers
CAS number	10534-44-8
PubChem	439351
ChemSpider	388474 Y
ChEBI	CHEBI:17947 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C1C[C@@](O)([C@@](O)=O)C[C@@H] (O)[C@@H]1O O=C1[C@@H](O)[C@H](O)C[C@](O)(C(=O)O)C1
InChI InChI=1S/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1 Y Key: WVMWZWGZRAXUBK-SYTVJDICSA-N Y InChI=1/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1 Key: WVMWZWGZRAXUBK-SYTVJDICBW
Properties
Molecular formula	C7H10O6
Molar mass	190.152 g/mol
Y acid (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

3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7. It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. 3-Dehydroquinic acid undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a precursor to tyrosine, 3-phenylalanine, tryptophan, and some vitamins, including:

• Vitamin K
• Pteroylmonoglutamic acid, called folate.

3-Dehydroquinate can also be a precursor to pyrroloquinoline quinone(PQQ), an alternate redox coenzyme involved in oxidative phosphorylation.

Biosynthesis

3-Dehydroquinate goes through beta oxidation, similar to fatty acids. Then, this compound (6-oxo-3-dehydro-quinate) is transaminated to 6-amino-3-dehydroquinate. Then 6-amino-3-dehydro-quinate is dehydrated and reduced to 6-amino-4-desoxy-3-keto-quinate, which reacts with dehydroalanine and alpha-ketoglutarate, to form hexahydro-pyrroloquinoline quinone. This compound is oxidized by FAD to PQQ.

References