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3-Dehydroquinic acid



3-Dehydroquinic acid
IUPAC name (1R,3R,4S)-1,3,4-trihydroxy-
5-oxocyclohexanecarboxylic acid
Identifiers
CAS number xx-xx-xx
SMILES O=C1C[C@@](O)([C@@](O)=O)C[C@@H]
(O)[C@@H]1O
Properties
Molecular formula C7H10O6
Molar mass 190.152 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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:

Additional recommended knowledge

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

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "3-Dehydroquinic_acid". A list of authors is available in Wikipedia.
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