3-Dehydroquinic acid

3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway.

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

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.

3-Dehydroquinic acid
3-Dehydroquinic acid