3-Dehydroquinic acid
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| 3-Dehydroquinic acid | |
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| IUPAC name | (1R,3R,4S)-1,3,4-trihydroxy- 5-oxocyclohexanecarboxylic acid |
| Identifiers | |
| CAS number | [xx-xx-xx] |
| PubChem | |
| 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 |
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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.
[edit] 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.
[edit] References
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