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3-Dehydroshikimic acid

3-DHS (−)-3-DHS

3-Dehydroshikimic acid is a chemical compound related to shikimic acid. 3-DHS is available in large quantity through engineering of the shikimic acid pathway.

Metabolism

Biosynthesis: The enzyme 3-dehydroquinate dehydratase uses 3-dehydroquinate to produce 3-dehydroshikimate and H2O.

3-Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor.

:[[Image:Shikimate pathway 2.png|left|500px|thumb|Biosynthesis of shikimic acid from 3-dehydroquinate]]

Gallic acid is also formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound spontaneously rearranges to gallic acid.{{Cite journal

References

(2003). "Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer". The Journal of Organic Chemistry.
[http://www.metacyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-6707 Gallic acid pathway on metacyc.org]
(2011). "Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia)". Plant Molecular Biology.

Info: Wikipedia Source

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