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.
Read more about 3-Dehydroquinic Acid: Biosynthesis