3-Dehydroquinic acid

3-Dehydroquinic acid
Identifiers
CAS number 10534-44-8
PubChem 439351
ChemSpider 388474 YesY
ChEBI CHEBI:17947 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H10O6
Molar mass 190.152 g/mol
 YesY acid (verify) (what is: YesY/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


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Look at other dictionaries:

  • quinic acid — l q.; the (−) isomer is an acid found in cinchona bark and elsewhere in plants; 5 dehydroquinic acid is an intermediate in the biosynthesis of l phenylalanine, l tyrosine, and l tryptophan from carbohydrate precursors; q. forms a γ lactone upon… …   Medical dictionary

  • Шикиматный путь — Шикиматный путь  метаболический путь, промежуточным метаболитом которого является шикимовая кислота (шикимат). Шикиматный путь наряду с поликетидным (ацетатно малонатным) механизмом построения бензольных ядер отмечается как… …   Википедия

  • 3-dehydroquinate synthase — In enzymology, a 3 dehydroquinate synthase (EC number|4.2.3.4) is an enzyme that catalyzes the chemical reaction:3 deoxy arabino heptulonate 7 phosphate ightleftharpoons 3 dehydroquinate + phosphateHence, this enzyme has one substrate, 3 deoxy… …   Wikipedia


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